l’actualité chimique canadienne canadian chemical news ACCN
APRIL | AVRIL • 2007 • Vol. 59, No./no 4
CNC/IUPAC Travel Awards
ANTIOXIDANTS Free Radicals on the Brain Rules for Natural Health
Gauging Material Efficiency Accreditation for Canadian Chemists
CIC Silver Medalists
ACCN
A publication of the CIC | Une publication de l’ICC
APRIL | AVRIL • 2007 • Vol. 59, No./no 4
Ta bl e o f C o n t e n t s | Ta bl e d e s m a t i è r e s
Ar ticles
Guest Column Chroniqueur invité . . . . . . 2 Aligned with Antioxidants Nam Fong Han, FCIC
10
Free Radicals on the Brain
14
Gauging Material Efficiency
18
The CSC Accreditation Program
Letters Lettres . . . . . . . . . . . . . . . 3
News Nouvelles . . . . . . . . . . . . . . 3
Hyman M. Schipper
John Andraos, MCIC
Patent Quest. . . . . . . . . . . . . . . . . 7
Chemfusion . . . . . . . . . . . . . . . . . 8 Joe Schwarcz, MCIC
John M. McIntosh, FCIC
Recognition Reconnaissance. . . . . . . . . 20
Events Événements . . . . . . . . . . . . . 26
Careers Carrières
. . . . . . . . . . . . . 28
Cover: concept and photography by Krista Leroux
GUEST COLUMN CHRONIQUEUR INVITÉ
Editor-in-Chief/Rédactrice en chef Michelle Piquette Managing Editor/Directrice de la rédaction Heather Dana Munroe Graphic Designer/Infographiste Krista Leroux
Aligned with Antioxidants
T
oday’s health conscious consumers pay attention to what they purchase and consume, and this has led to the creation of a class of foods referred to as nutraceuticals. Nutraceutical foods provide specific nutritional components and are believed to deliver certain health and medical benefits that may include the prevention and treatment of cancer and other diseases. Many consumers have been exposed to the term “antioxidants,” and there is a high demand for incorporating these compounds into our diets. Synthetic classical antioxidants—free radical scavengers such as butylated hydroxyl toluene (BHT), propyl gallate (PG), and tertiary butyl hydroquinone (TBHQ)—are widely used in food preparations, but their safety is subject to periodic review. Informed consumers tend to prefer natural antioxidants to synthetics, as the former are generally derived from dietary sources and are closely related to familiar foods they consider to be safe. An antioxidant’s role is to inhibit the process of lipid oxidation. In foods, oxidation is likely to cause a loss of organoleptic and nutritional quality of the product, and therefore a loss of economic value. Factors such as smoking, exposure to pollution, and poor eating habits may contribute to the oxidation processes, thus creating undesirable amounts of damaging free radicals that can overwhelm our innate defence mechanisms. Naturally occurring antioxidants, such as Vitamin C and Vitamin E, have been widely promoted in nutraceutical foods. Natural antioxidants derived from the plant kingdom have become part of the trend. These materials such as extracts of grape seed, green tea, wild berries, and pomegranate can be found in many formulations. Most recently, coffee, chocolate, and flaxseed have received a great deal of
2 L’ACTUALITÉ CHIMIQUE CANADIENNE AVRIL 2007
Nam Fong Han, FCIC
attention as functional foods and valuable sources of antioxidants. As far back as 5000 BC, people have eaten flaxseed. Since then, praise of its benefits has been revived. Canada is the world leader in the production and export of this seed. It is one of the five major Canadian crops. Flaxseed is very high in omega-3 fatty acid as well as many phytochemicals that appear to possess antioxidant, anti-cancer, and antimicrobial activities. Flaxseed is one of the richest sources of a plant lignan called secoisolariciresinol diglycoside (SDG). SDG is an antioxidant as it can scavenge certain free radicals such as the hydroxyl ion. Free radicals are known to damage tissues and have been linked to many diseases. The antioxidant action of SDG was studied and was found to be greater than that of Vitamin E (α-tocopherol) in some studies. However, there is insufficient human trial data to recommend a specific daily dose of flax lignan. Analytical methods for determining the antioxidant activities in natural compounds including flaxseed SDG are still not well established. Known methods include the active oxygen method (AOM) and its automated versions (Rancimat and SAFTEST) for lipophilic phases, and 2,2-Diphenyl-1-picrylhydrazyl (DPPH) or oxygen radical absorption capacity (ORAC) for aqueous environments. The extent of the role of flaxseed SDG in fighting disease should be carefully studied to establish the full benefits of this important Canadian crop. However, we can fairly assess that consuming a diet rich both in flaxseed and in other antioxidant-rich foods such as fruits and vegetables has historically been a smart decision.
Editorial Board/Conseil de rédaction Joe Schwarcz, MCIC, chair/président Cathleen Crudden, MCIC John Margeson, MCIC Milena Sejnoha, MCIC Steve Thornton, MCIC Bernard West, MCIC Editorial Office/Bureau de la rédaction 130, rue Slater Street, Suite/bureau 550 Ottawa, ON K1P 6E2 613-232-6252 • Fax/Téléc. 613-232-5862 editorial@accn.ca • www.accn.ca Advertising/Publicité advertising@accn.ca Subscription Rates/Tarifs d’abonnement Non CIC members/Non-membres de l’ICC : in/au Canada CAN$55; outside/à l’extérieur du Canada US$50. Single copy/Un exemplaire CAN$8 or US$7. L’Actualité chimique canadienne/Canadian Chemical News (ACCN) is published 10 times a year by The Chemical Institute of Canada / est publié 10 fois par année par l’Institut de chimie du Canada. www.cheminst.ca. Recommended by The Chemical Institute of Canada, the Canadian Society for Chemistry, the Canadian Society for Chemical Engineering, and the Canadian Society for Chemical Technology. Views expressed do not necessarily represent the official position of the Institute, or of the societies that recommend the magazine. Recommandé par l’Institut de chimie du Canada, la Société canadienne de chimie, la Société canadienne de génie chimique et la Société canadienne de technologie chimique. Les opinions exprimées ne reflètent pas nécessairement la position officielle de l’Institut ou des sociétés constituantes qui soutiennent la revue. Change of Address/Changement d’adresse circulation@cheminst.ca Printed in Canada by Gilmore Printing Services Inc. and postage paid in Ottawa, ON./ Imprimé au Canada par Gilmore Printing Services Inc. et port payé à Ottawa, ON. Publications Mail Agreement Number/ No de convention de la Poste-publications : 40021620. (USPS# 0007-718) Indexed in the Canadian Business Index and available on-line in the Canadian Business and Current Affairs database. / Répertorié dans la Canadian Business Index et accessible en ligne dans la banque de données Canadian Business and Current Affairs. ISSN 0823-5228
Nam Fong Han, FCIC, is president and CEO of Natunola Health, which supplies biological alternatives to petroleum-based ingredients in cosmetics and health care.
www.accn.ca
NEWS NOUVELLES
LETTERS LETTRES
GRAPE DIVIDE I am a fan of Joe Schwarcz’s “Chemfusion,” but I would like to mention a little mistake in the February 2007 column. He said that “ ... resveratrol, which is found more extensively in red grapes than in white, is responsible.” Resveratrol is mainly present in the skin of the grapes. There is less resveratrol in white wine than in red wine because in the preparation of white wines, the skins are removed. In red wines, the skins are not removed. That is why there is much more resveratrol in red wines. Please note that this “incident” won’t change my eagerness to read “Chemfusion” each month. Benoit Daoust, MCIC PEER REVIEW? Giving “activists,” businesses, and governments a voice in the ACCN magazine may enhance ACCN’s journalistic credibility or it may harm that credibility unless the information is presented in context and with any uncertainty noted as an “Editor’s Comment” or similar sort of peer review. Perhaps the CIC could set itself up as the peer review standard for chemical science published in the consumer press. For a fee charged by the CIC to those seeking the credibility of the CIC imprimatur, CIC members with the expertise could be engaged by the CIC to do the reviews. Paul Larocque, MCIC
What Do You Think? editorial@accn.ca
Prominent American Nanotechnology Researcher Recruited to Canada A leading American chemist, working in the field of molecular scale electronics, has been enticed to Alberta to continue his groundbreaking research on new microelectronic platforms. “I am excited about coming to a place that puts such a high priority on research and development,” said Richard McCreery, MCIC. “I was not looking to leave Ohio, but the situation and opportunities here were hard to resist.” McCreery has relocated to Alberta from The Ohio State University in Columbus, OH. Coming north to continue his research in Edmonton, AB, at the National Research Council Canada (NRC)’s National Institute for Nanotechnology (NINT) as a principal researcher and ingenuity scholar, he will also teach chemistry at the University of Alberta. Doug Horner, Minister of Advanced Education and Technology, believes that new electronic business opportunities in Alberta are not far off because, “McCreery’s research could lead to significant improvements in electronics and computing.” He added, “Moving ideas developed in the lab into products and processes for markets relevant to our province, reflects our government’s priority to build a stronger Alberta.” McCreery’s research will investigate the behaviour of molecules or single molecular layers as electronic circuit components, with the goal of developing new technology platforms for microelectronics. Molecular circuit components are potentially more versatile than existing microelectronics, and may lead to reduced cost and lower power consumption. Funding partner Peter Hackett, president and CEO of Alberta Ingenuity, said, “This is how we create benefits for Alberta in nanotechnology—get exceptional people, provide exceptional support, so they create exceptional results. We are delighted to support the recruitment of innovators like McCreery to the province.” Gregory Taylor, dean of science at the University of Alberta, is thrilled that McCreery will be a professor in the department of
chemistry. “Not only will we benefit from McCreery’s innovative and extensive research program, but he will be instrumental in integrating research into the learning environment to enhance the undergraduate and graduate student experience.” McCreery’s research and academic efforts will be supported during the next five years by a total of $4.5 million in funding from the National Research Council Canada ($2.5 million), the Alberta Ingenuity Fund ($1 million), and the University of Alberta ($1 million). In welcoming the fellow chemist, Nils Petersen, FCIC, director general of NINT, said, “Our ability to recruit an established scientist like Rick McCreery shows that partnership between the NRC, the University of Alberta, and the Government of Alberta can compete in attracting research excellence in strategically important areas.” NINT
2007 Canadian Chemical Directory Camford Information Services is pleased to announce that the 2007 Canadian Chemical Directory is now available. This directory is the most comprehensive listing of suppliers of feedstocks, intermediates, minerals, metals, resins, and pharmaceuticals in Canada. The Companies section provides an alphabetical listing of approximately 570 chemical manufacturers and distributors, listing addresses, telephone and fax numbers, e-mail addresses, executives, sales contacts, manufacturing plants, branch sales offices, parent and subsidiary companies, principals (foreign firms represented in Canada), chemical products, and trade names. The Products section lists over 3,300 chemical products, showing which companies supply each product and indicating whether they manufacture in this country. Additional sections provide cross-referenced listings for parent companies, subsidiaries, principals and trade names. The price for the 2007 edition is $160, plus taxes. Order forms can be downloaded at www. camfordinfo.com. Please send orders to Bob Douglas at bdouglas@camfordinfo.com. Camford Chemical Report
APRIL 2007 CANADIAN CHEMICAL NEWS 3
NEWS NOUVELLES
University of Manitoba president and vice-chancellor Emöke Szathmáry (left) accompanies Rod Bruinooge, MP for Winnipeg South, on a tour of the chemistrylabs.
The Chemistry Centre of Excellence An outdated chemistry lab in the Parker Building at the University of Manitoba (U of M) will soon be transformed into a 21st century research and training facility for students, graduates, and local companies. Plans for the Chemistry Centre of Excellence were announced in January by Rod Bruinooge, MP for Winnipeg South, on behalf of Rona Ambrose, then minister of intergovernmental affairs and minister of western economic diversification, and Emöke Szathmáry, president of the U of M. Surrounded by the outmoded lab paraphernalia that Bruinooge lightheartedly referred to as “Cold War technology,” the MP announced that the federal government was investing $555,000 into the project. “The new centre will educate students, train professionals, and conduct research that is critical for the next generation of biotech professionals,” said Bruinooge. Szathmáry echoed the minister’s thoughts, pointing out that the scientists and engineers of tomorrow cannot be trained on the equipment of yesterday.
4 L’ACTUALITÉ CHIMIQUE CANADIENNE AVRIL 2007
“The University of Manitoba is delighted to work in partnership with the federal government and industry to improve the learning and research capabilities of this lab,” Szathmáry said. “Equipment, ventilation, and instrumentation upgrades will provide our students and local industry with the most up-to-date equipment on which to hone their skills and develop new technologies.” The funds announced in January will be used to purchase and install new instrumentation equipment and provide continuing education opportunities for professionals. The new equipment will also provide research capabilities for local industry that were not possible because of aging infrastructure. “Modern, state-of-the-art laboratories are essential to provide the level of education and hands-on experience required to create a strong workforce,’’ said Michael Freund, MCIC, associate professor of chemistry at the U of M and Canada Research Chair in conducting polymers and electronic materials. “Once completed, this facility will be the most modern and advanced undergraduate laboratory of its kind in the region and will expose our students to leading-edge technology that will increase their competitiveness in the job market, as well as their ability to increase innovation within the province.” Manitoba’s biotechnology sector contributes $400 million to the provincial economy and employs approximately 5,000 people. Its activities are complemented by the province’s strong manufacturing sector. The demand for employees in both areas is expected to continue growing. Representatives from the departments of chemistry and geological sciences, industry, and government will form an advisory board to ensure the Chemistry Centre of Excellence remains responsive to industry needs. The board will provide the direction and activities, such as equipment purchases. A research board will guide research initiatives. Total project cost is estimated at $1.03 million, with the remaining funds provided by the University of Manitoba and in-kind contributions by industry. Western Economic Diversification Canada’s investments in the U of M include such projects as the Nano-Systems Fabrication Laboratory ($1.24 million), university’s engineering labs ($1.065 million), and Smartpark ($2.1million). University of Manitoba Bulletin
Praxair Acquires Blue Rhino Assets Praxair Distribution, a division of Praxair Canada, has acquired the Canadian propane tank exchange business of Blue Rhino, a Ferrellgas Partners company. Under the agreement, Praxair acquired over 900 propane tank exchange display cages at retail locations across Canada. In addition, it will take over the contract to supply more than 300 retail gasoline stations belonging to Shell Canada Products with 20 pound propane tanks for their exchange program. In conjunction with this transaction, Praxair signed a distributor agreement with Superior Tank, which will serve Praxair’s propane tank-exchange customers in the Atlantic provinces. Previously, Praxair provided propane tank filling and distribution services for Blue Rhino retailers in the six largest provinces of Canada. Now, Praxair will not only fill the tanks but will also market propane tank exchange under its own trademark, PropaneQuikSwap, in all ten provinces. “With six propane fill plants serving Canada, we are uniquely positioned to service the 20 pound propane tank-exchange market,” said Pat Heffernan, vice-president and general manager for Praxair Distribution. Camford Chemical Report
Available: NRC Journal Back Files Back files of six NRC Research Press journals are available for one-time purchase: • Canadian Journal of Chemistry • Canadian Journal of Forest Research • Canadian Geotechnical Journal • Canadian Journal of Civil Engineering • Canadian Journal of Botany • Canadian Journal of Physics There are no annual maintenance fees and access is perpetual. The regular price for each journal back file is $2,000, but early bird and bundled discounts are available. For more information, contact Mike Boroczki at mike. boroczki@nrc-cnrc.gc.ca. National Research Council Canada
Photo by Michael Marshall
NEWS NOUVELLES
Rules for Natural Health Since 2004, Canada has required that natural health products be labelled with standard information such as quantity, dosage, route of administration, possible adverse reactions, and storage conditions. Although this puts more information at consumers’ fingertips, an Advanced Foods & Materials Network
(AFMNet) research team is studying just how effectively the knowledge is being used. Led by Heather Boon, professor of the Leslie Dan Faculty of Pharmacy at the University of Toronto, the team is studying consumer awareness of the new regulations and how they’re making use of the information. Boon is also gauging how well pharmacists are trained to help consumers with natural health products. “We want to know how the new health product regulations are affecting
Canadians—not only consumers but also practitioners, pharmacists, and natural health product companies,” she says. The study is looking at over-the-counter herbal and homeopathic remedies, vitamins, minerals, and essential fatty acids. The research team has already assessed how the new regulations have affected complementary medicine practitioners (such as herbalists and naturopaths) and companies that manufacture, import, and sell natural health products. Data analysis is now under way. Next, they’ll study the impact on consumers and pharmacists. Focus groups held across Canada asked questions such as how pharmacists were expected to give advice on natural health products. Boon says that although pharmacies are carrying abundant amounts of natural products, pharmacists may not be trained in natural medicine and may be unable to answer consumer inquiries. A survey will be sent to pharmacists in early spring to determine their level of natural product knowledge and customer support. It will focus on their current knowledge of natural health products, what they’re doing and what other support they need to improve their service abilities. Boon hopes to use the gathered information to enrich pharmacy training programs and initiate changes to the educational system that include more information on natural health products. “We plan to work to change the educational system and training so pharmacists can better meet the needs of consumers.” Researchers involved in this project hail from the University of Alberta, The University of British Columbia, Dalhousie University, the University of Guelph, the University of Manitoba, and the University of Toronto. This research is funded by AFMNet and the Canadian Institutes of Health Research. Lindsay Brown, AFMNet ADVANCE
Question?
Patent
patentquest@accn.ca
APRIL 2007 CANADIAN CHEMICAL NEWS 5
NEWS NOUVELLES
Investigating Biodiesel Blends
Chemicals Management Plan
A group of diverse stakeholders, with an interest in gathering comprehensive data about the quality requirements of biodiesel blends used in Canada, are announcing their intention to embark on a two-phase biodiesel pilot project in anticipation of a federal renewable fuels strategy. The demonstration pilot is a joint undertaking of the Canadian Renewable Fuels Association and the Canadian Petroleum Products Institute. Barb Isman, president of the Canola Council of Canada, supports the pilot. “We need this new industry, which represents several million tonnes of oils and fats demand, to be sustainable over the long term. This pilot project is critical in starting off on the right foot with the end-users of biodiesel in Canada.” The project will address the primary fuel quality areas of interest related to the adoption of biodiesel.
In December 2006, the federal government announced a new plan for the management of chemicals in Canada. There are a number of facets to this plan that are summarized below. Since 1994, the manufacturing or import of new chemicals into Canada has been subject to the New Substances Notification (NSN) regulations. These require that companies provide data to Environment Canada and Health Canada so that these co-administrators of the NSN can decide whether or not there are health or environmental concerns pertaining to the new chemical. However, there was a legacy list of 23,000 chemicals, known as the Domestic Substances List (DSL), that were in commerce prior to the introduction of the NSN regulations. These substances had not been subject to any formal screening criteria. In the fall of 2006, Environment Canada and Health Canada completed their review of the substances on the DSL. The review examined their persistence in the environment, tendency for bioaccumulation, inherent toxicity, and potential for exposure to the population. A number of follow-up actions resulted from that review. There were 60 substances for which the government announced plans to initiate actions to prohibit their manufacture or import into Canada. These include a family of polybrominated diphenylether flame retardants (PBDE), perfluorooctane sulfonate (PFOS) and its salts and its precursors used in non-stick coatings and repellants, pentrachlorobenzenes, tetrachlorobenzenes, and 2-methoxyethanol. There were another 200 substances of high priority for assessment identified. The intent is to challenge industry to provide information on these substances to prove that they are being used in a manner that does not compromise human health or the environment. These challenges will be done in batches of 15 to 30 chemicals every 3 months. Industry will have 6 months to provide input. In cases where no input is received, or where Environment Canada and/or Health Canada deems the information non-convincing, these substances will be slated for listing on Schedule 1 of the Canadian Environment Protection Act (CEPA 99). From there, they could progress to prohibition or risk management plans, as appropriate.
Canadian Bioenergy Corporation
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6 L’ACTUALITÉ CHIMIQUE CANADIENNE AVRIL 2007
There were another 148 substances identified that would have been a high priority to assess, but according to government information, these are not currently in commerce in Canada. These substances will stay on the DSL, but with a significant new activity (SNAc) flag attached to them. The government would need to be advised, and provide permission, before these substances could be used again in Canada. There were another 150 substances that posed concern to human health. The government will ensure exposures do not increase by applying limits on their future use. There were 1,200 substances of lower concern that nonetheless met some of the categorization criteria. These will be subject to a rapid screening risk assessment to determine which of the 1,200 are truly in need of additional study. It is expected that the majority will be found to pose no risk. One substance, hexachlorobutadiene, will become the first to be placed on the Virtual Elimination list, meaning that it will become the intent of the government to reduce releases to levels below the measurable limit, also taking into account social, economic, technical, and risk considerations. One substance, 2-butoxyethanol, used in cleaning and paint products, will have restrictions placed on its use. Changes to the Pest Control Products Act include the re-evaluation of 200 older pesticides according to newer, more stringent health and environmental standards. More detailed information about the plan can be found at www.chemicalsubstances.gc.ca While not part of the Chemical Management Plan, a closely allied initiative is an intent to remove 1,105 substances from the DSL because they did not meet the necessary conditions for placement on the list in the first place, in the view of government. If companies believe substances have been placed in this group in error, they have 6 months to provide information to demonstrate that these substances qualify to remain on the DSL. Details on the options that exist for companies accompanied the notice in Canada Gazette I on November 11, 2006 and can be accessed at www. canadagazette.gc.ca/partI/2006/20061111/ html/index-e.html. Industry Canada
NEWS NOUVELLES
Quest
Patent
Lawyer and patent agent, Daphne C. Lainson, MCIC, answers your questions on patenting your discoveries. Send your questions to patentquest@accn.ca.
Q: I developed a new sweetener for use in a toothpaste. I worked on developing the sweetener with a colleague. I am interested in patenting the sweetener, but my colleague is not. Can I go ahead without him?
Goodyear Plant Re-Tires The Goodyear Tire & Rubber Company will discontinue tire production at its facility in Valleyfield, QC. The company plans to convert the Valleyfield facility to a materials mixing centre by the end of the second quarter of 2007. The reduction in both capacity and labour in Valleyfield is related to the company’s ongoing global strategy to reduce excess high-cost manufacturing capacity. “In today’s intensely competitive and increasingly global business environment, we face some very difficult choices,” said Jon Rich, president of Goodyear’s North American Tire business. “The decision to discontinue tire production at Valleyfield is one of those necessary steps to make Goodyear more competitive. This decision does not reflect on the commitment or performance of our Valleyfield associates.” The company will continue to make tires in Canada at plants in Napanee, ON, and Medicine Hat, AB.
A: The first question to ask is whether you are both inventors. In general, an inventor is a person who contributed to the invention as defined by the claims of a patent specification. It is not always easy to determine inventorship, and you want to get it right. In the U.S., for example, if inventors are not correctly named, the patent may be found invalid. Thus, if your colleague is an inventor, he or she must be named as an inventor. Some countries require legal forms to be signed in order to proceed in obtaining a patent. If your colleague refuses to sign, there are usually procedures that can be followed to allow you to advance the application alone. If your colleague is not an inventor, then you will likely be able to proceed in obtaining a patent without his or her involvement. In either case, before proceeding you should consider whether your colleague, or any other party, might irrespective of inventorship have an ownership interest in your invention. It would be wise to sort out any ownership issues before investing in the preparation and filing of a patent application for which you may not obtain the benefit because you do not own the whole of the invention. Daphne C. Lainson, MCIC, is a lawyer and patent agent with the law firm Smart & Biggar in Ottawa, ON. Smart & Biggar is Canada’s largest firm practising exclusively in intellectual property and technology law. Disclaimer: The preceding is intended as informational only, and does not constitute professional advice.
The Goodyear Tire & Rubber Company
APRIL 2007 CANADIAN CHEMICAL NEWS 7
CHEMFUSION Joe Schwarcz, MCIC
THE ANTIOXIDANT DEFENCE
I
n the 1950s, Denham Harman began to study the effects of radiation on mice. He noted that the animals aged more quickly and had a reduced life expectancy. This could happen, he theorized, if the radiation sparked the production of some highly reactive and destructive chemical species that then went on to wreak havoc in tissues. At the time, Harman’s idea did not generate much interest, but it wasn’t long before the scientific world began to vigorously debate the existence of his rogue “free radicals.” Free radicals, Harman suggested, could be tamed. In fact, food processors were already doing this by adding certain preservatives to their products. Butylated hydroxy toluene, or BHT, was commonly used to prevent fat from going rancid. This worked, Harman said, because the rancidification of fat was a reaction mediated by free radicals that were neutralized by BHT. He added BHT to the diet of rats and showed that their life expectancy increased. However, there being no practical evidence for free radical damage, the scientific community remained skeptical until 1969. It was then that an enzyme called superoxide
8 L’ACTUALITÉ CHIMIQUE CANADIENNE AVRIL 2007
dismutase (SOD) was discovered in cells. Apparently its sole function was the destruction of a type of free radical known as superoxide. Why would this enzyme be present in all cells if free radicals did not represent a danger? Research into free radicals accelerated. A newly developed instrumental technique known as electron spin resonance showed that they did indeed exist in biological systems. Soon free radicals were being linked with heart disease and cancer—the major diseases that shorten our lives. How does this happen? Scientifically speaking, “life” is just the result of all the simultaneously occurring chemical reactions in our bodies. Some of these reactions are involved in building muscle, some in destroying invading bacteria, some in growing hair, some in synthesizing sex hormones, and some in fostering our thought processes. Then there are the reactions that generate the energy required to fuel all of the other processes. And therein lies the problem. Life is actually deadly! The same reactions that produce the energy allowing us to carry on with our lives also create the insidious free radicals that may hasten our demise. Just as a furnace burns oil for energy, our cells burn glucose. And for this combustion process to take place—like the furnace—our cells need a constant supply of oxygen. The oxygen is absorbed through the lungs, incorporated into hemoglobin molecules in red blood cells, and delivered by the bloodstream to the trillions of microscopic furnaces we call cells. Here, the oxygen begins the process of deriving energy from glucose by breaking the chemical bonds that hold the molecules together. Chemical bonds are nothing more than a pair of electrons between the atoms that are joined together. Oxygen strips an electron from glucose and thereby disrupts the “glue” holding the molecule together. This in turn begins the cascade of events that ultimately converts glucose into carbon dioxide and water, releasing energy in the process. Now the oxygen molecule is stuck with an extra electron. An unfulfilled chemical bond, as it were. It has become a free radical, desperately searching for some molecule with which it can react to satisfy its craving for electrons. And there are plenty of candidates in that cellular chemical stew. Fats and proteins, for example, are readily “oxidized.” So is deoxyribonucleic acid, or DNA, the master control molecule of life.
Unfortunately, when these compounds sacrifice themselves to appease the reactive oxygen, they are altered in such a way that they can no longer fulfill their function. Certain proteins lose their elasticity and our skin wrinkles. Other proteins, responsible for carrying cholesterol around the bloodstream, are oxidized to a form that damages arteries, potentially causing coronary disease. The fats in cell membranes may become rancid—shortening the cells’ lives. Worst of all, damage to DNA molecules that control the multiplication of cells can cause cancer. It is not a pretty picture.
Our bodies do not take the free radical onslaught lying down. There are yet other ways in which free radicals can form. Certain white blood cells produce them as weapons against invading organisms, but unfortunately, healthy tissues may suffer from “friendly fire” and inflammation results. Sunlight, X-rays, and environmental pollutants like ozone can also trigger free radical formation. Given this dark scenario, how is it that we actually survive at least for a while? Because our bodies have remarkable defence weapons—the “antioxidants.” Our bodies do not take the free radical onslaught lying down. Cells respond by synthesizing enzymes like superoxide dismutase and glutathione peroxidase that destroy free radicals. And then there are the all important, highly publicized, dietary antioxidants. Vitamin C, Vitamin E and beta carotene can all dissipate a free radical’s destructive appetite by happily absorbing its extra electron. We are not only talking esoteric theory. Study upon study suggests that we can improve our prospects for health by increasing our intake of foods rich in these antioxidants. The lingering question that lurks in a chemist’s mind, however, is whether or not we have oversimplified the whole antioxidation scenario by undue emphasis on Vitamin E, Vitamin C, and beta carotene. After all, food is an incredible collage of chemicals. Isn’t it likely that the beneficial effects noted for fruit and vegetable consumption are the result of cohesive teamwork? Michael Jordan, as great as he was, could not bring home a championship until he had a sufficiently strong team behind him. So it may be with
… continues on p. 27
FREE RADICALS ON THE BRAIN Hyman M. Schipper
Redox biomedicine: a rapidly emerging discipline
R
ecent years have witnessed a tsunami of new knowledge implicating free radicals and oxidative stress (OS) in virtually every aspect of biology and medicine. At “physiological” concentrations, reactive oxygen species (ROS) may play adaptive roles as signalling molecules involved in gene regulation, cell growth, differentiation, replicative senescence and apoptosis (cell death), and as a primary defence invoked by white blood cells against invading organisms. Moreover, in conditions as disparate as ischemic heart disease, inflammatory bowel disease, cataract formation, immune-mediated kidney damage, asthma, cancer, diabetes mellitus, and infertility, OS is being increasingly recognised as a key common pathway for cellular death and dysfunction, and a potentially important target for therapeutic intervention.
Oxidative stress: chemical warfare on a biological battlefield Free radicals are atoms or molecules that contain unpaired electrons in their outermost orbitals. Their electronic configurations render these chemical species highly reactive with a host of cellular substrates, notably proteins, lipids and nucleic acids. Free radicals may be derived from environmental sources or they may be generated de novo within tissues. Examples of common, endogenously produced free radicals and non-radical pro-oxidants include singlet oxygen, the superoxide anion (O2-), hydrogen peroxide (H2O2), peroxynitrite (ONOO-), hypochlorous acid (HOCl), and the hydroxyl radical (OH•). Transition metals, such as ferrous iron (Fe2+) or cuprous copper (Cu1+), play a pivotal role in cellular redox chemistry by reducing H2O2 to the highly toxic OH• radical (Fenton catalysis). Transition metals may also promote the degradation of lipid hydroperoxides within cell membranes, or behave as non-enzymatic (pseudo-) peroxidases capable of converting innocuous catechol-containing compounds (such as the neurotransmitter, dopamine) to toxic ortho-semiquinone intermediates. Organisms representing all phyla surveyed to date are endowed with a host of evolutionarily conserved defence mechanisms designed to either prevent free radical production in situ, scavenge reactive oxygen species (ROS) generated within various aqueous and hydrophobic cellular domains, or repair oxidative chemical damage once incurred. In mammalian tissues, key antioxidant enzymes include the superoxide dismutases (disproportionate O2- to H2O2 and O2), catalase, the glutathione peroxidases and the peroxiredoxin complex (neutralize H2O2 to water), and various reductases that help replenish stores of the major intracellular electron donors (reduced glutathione, reduced thioredoxin) that become depleted in the course of peroxidase and oxidoreductase reactions. The antioxidant enzymes operate in collusion with a host of non-enzymatic, low-molecular-weight antioxidant compounds (e.g. glutathione, ascorbate, the tocopherols, uric acid, melatonin, and bilirubin) to preserve tissue redox homeostasis. By maintaining transition metals in a relatively low-redox state, metal-binding proteins, including ferritin, transferrin, the metallothioneins, and ceruloplasmin, contribute significantly to the antioxidant protection of tissues and body fluids. OS has been defined by Helmut Sies (1991) as “a disturbance in the pro-oxidant/antioxidant balance in favour of the former, leading to possible [tissue] damage.” Although usually implying the
participation of ROS per se, oxidative stress may be construed to also encompass the deleterious interactions of sulphur-derived thiyl radicals (sulfhydryl stress) and nitrogen-based radicals (nitrosative stress) with biochemical substrates.
Neurological damage by free radical assault OS has been implicated in a broad range of disorders affecting the central and peripheral nervous systems. In a position paper published in the Annals of the New York Academy of Sciences (Vol. 1012, 2004), I defined “Redox Neurology” as the study of the roles of free radicals, transition metals, oxidative stress, and antioxidant defences in diseases of the nervous system. The exponential rise in numbers of published experimental and clinical reports related to the “redox neurosciences” over the last decade or so attests to the burgeoning interest in this field. Why the brain? Although free radical injury has been implicated in diseases involving virtually every organ system, there are numerous biochemical and physiological factors that render the CNS particularly prone to oxidative damage: 1. Although the human brain represents only 2 percent of total body mass, it is responsible for ~20 percent of total O2 consumption under basal conditions. 2. The brain is replete with unsaturated fat (e.g. C20:5, C22:6) and is thus highly vulnerable to lipid peroxidation. 3. Relatively high concentrations of total and free transition metals (mainly Fe and Cu) in the CNS predispose to Fenton-mediated hydroxyl radical formation and cytotoxicity. Iron is indispensable for normal neural development and physiology and contributes to a diverse spectrum of cellular functions including myelination, biogenic amine metabolism, electron transport, antioxidant enzyme activity, and cell proliferation. To facilitate these vital functions, while at the same time limiting the metal’s propensity to mediate toxic Fenton reactions (vide supra), iron homeostasis in neural and other tissues is tightly controlled by an orchestra of proteins governing the absorption, valence configuration, extracellular transport, cellular flux, chemical signalling activities, and intracellular storage of the metal. Despite this elaborate control, iron accumulates in the mammalian CNS as a function of advancing age, and a portion of the metal in the brain substance and cerebrospinal fluid is maintained in a redox-active state. OS resulting from perturbations in the levels or distribution of brain Fe and Cu has been implicated in an impressive array of genetic and acquired neurological disorders, including such entities as Friedreich ataxia, pantothenate kinase-2-associated neurodegeneration (formerly Hallervorden-Spatz disease), neuroferritinopathy, Alzheimer disease, Parkinson disease, multiple sclerosis, aceruloplasminemia, superficial siderosis, the restless legs syndrome, and Wilson disease. Indeed, clinical trials are currently in progress to ascertain the potential therapeutic value of metal chelators (e.g deferoxamine, deferiprone, clioquinol) and high-dose antioxidants (e.g. vitamin E, N-acetylcysteine, CoQ10, idebenone) in several of these conditions—most notably, Alzheimer disease, Parkinson disease, and Friedreich ataxia. 4. Neural tissues are also enriched for low-molecular-weight compounds, such as dopamine, norepinephrine, and 3-hydroxykynurenine, which readily yield ROS via spontaneous and metal-catalyzed autoxidation reactions. Such mechanisms have
APRIL 2007 CANADIAN CHEMICAL NEWS 11
been implicated in the pathogenesis of Parkinson disease, and, to a lesser extent, schizophrenia and depression. 5. Under conditions of ischemia-reperfusion (stroke), trauma, or epilepsy, various signalling pathways and enzymes activated by the massive release of the excitatory amino acid, glutamate promote free radical generation and injury in target neurons as part of a so-called “excitotoxicity” cascade. 6. A dearth of antioxidant enzymes and other defences (relative to other tissues) further enhances the susceptibility of the nervous system to oxidative injury. In this regard, neural tissues are prime targets of oxidative damage accruing from metabolic disorders such as vitamins E and B12 deficiency, diabetes mellitus, and certain porphyrias (disorders of heme biosynthesis). In addition to remissions or clinical stabilization resulting from correction of the underlying metabolic derangement, there is some evidence of further therapeutic benefits from concomitant antioxidant supplementation (e.g alpha-lipoic acid for diabetic neuropathy). In rare instances, devastating disease may arise as a direct consequence of mutations in genes coding for antioxidant enzymes. The most notorious example of this in human neurology are familial forms of amyotrophic lateral sclerosis (Lou Gehrig’s disease) secondary to mutations in the copper-zinc superoxide dismutase gene on chromosome 21. In Down syndrome (trisomy 21), the mental retardation and later dementia may be due, in part, to excessive production of H2O2 resulting from a 50 percent increase in the level of brain copper-zinc superoxide dismutase (a gene dosage effect arising from triplication of chromosome 21) unmatched by compensatory rises in catalase or glutathione peroxidase. 7. Under normal conditions, ~1- 3 percent of molecular oxygen consumed by respiring mitochondria (the power generators of eukaryotic cells), is converted to O2- and thence to other, more damaging free radical intermediates. As such, mitochondria are arguably the single most important endogenous source of ROS. Mitochondrial ROS production increases substantially in aging and diseased tissues, particularly in post-mitotic cells such as neurons, cardiomyocytes, and skeletal muscle. It is therefore not surprising that rare disorders
12 L’ACTUALITÉ CHIMIQUE CANADIENNE AVRIL 2007
stemming from mutations in the mitochondrial genome, such as MERRF, MELAS, and the Kearn-Sayre syndrome, predominantly compromise the CNS, heart, and skeletal muscle. Mitochondrial free radical production also figures centrally in the development of Alzheimer disease, Parkinson disease, and other human neurodegenerations, and here the link to normal brain aging is paramount. Of the many theories of aging promulgated over the last several decades, the “Free Radical-Mitochondrial” theory remains among the most successful. In the mid-1950s, Denham Harman, an inorganic chemist-turned-biologist at the University of California (Berkeley), was the first to posit that “free radical reactions are involved in the aging changes associated with the environment, disease, and intrinsic aging processes.” In its current form, the theory states that oxidative injury to mitochondria, triggered by intrinsic metabolic processes and/or environmental insults, results in a cascade of events characterized by infidelity of electron transport and a selfsustaining spiral of augmented free radical generation within the inner mitochondrial membrane. The latter, in turn, engenders bioenergetic failure (depletion of ATP, the chemical energy “currency” of the cell) and progressive tissue aging. The model presupposes that any disease or injury that exacerbates mitochondrial ROS production could, theoretically, accelerate senescence of the affected tissue or organ. Conversely, normal aging tissues compromised by an increasingly unfavourable mosaic of healthy and ROS-spewing mitochondria (a situation termed “heteroplasmy”) may become particularly susceptible to aging-associated conditions such as atherosclerosis, neurodegeneration, and cancer. It is therefore the belief of many (this author among them) that a singularly promising way to cope with the looming Alzheimer “epidemic” and other senescence-dependant neurodegenerative disorders is to attenuate the rate of brain aging processes. Curtailment of brain ROS production by effete mitochondria, using appropriate cocktails of brain-permeable antioxidants, iron chelators, and mitochondrial protectants (e.g. l-carnitine)—perhaps in the context of adequate exercise (physical and mental) and moderate caloric restriction—may be one approach to realizing this critical imperative.
An appeal to chemists! As implied by this article in reference to the neurosciences, the field of redox biomedicine presents an outstanding opportunity for innovative collaboration among biologists, chemists, and clinicians. Chemists—whether physical or organic, applied or theoretical— are ideally poised to propel this discipline forward by offering a conceptual framework of the fundamental principles underpinning the science, and providing the analytical tools for robust data acquisition and interpretation. Illustrative of the myriad contributions conceivable here, the chemist’s expertise would be highly valued in the following areas: • application of highly specialized instrumentation, e.g. electron paramagnetic resonance spectroscopy, to disclose salient free radical pathways responsible for given pathologies; • delineation of structure/function relationships for normal and mutant antioxidant enzymes and their roles in health and disease; • assistance in the development of bioimaging technologies and non-invasive chemical biomarkers to monitor transition metal deposition and oxidative metabolism in situ; and perhaps most importantly; • development of “designer” antioxidants and metal chelators that safely and effectively target the CNS and other specialized body compartments. Free radicals have been implicated in a broad spectrum of normal and abnormal neurological (and other organ) functions. Involvement of OS and aberrant transition metal homeostasis in normal brain aging and in the development of many neurological conditions has become widely accepted in recent years in light of accumulating clinical, pathological, and biochemical data. A more thorough understanding of the mechanisms mediating OS-related neural dysfunction—an objective begging the input of theoretical and analytical chemists—should facilitate the refinement of rational antioxidant and metal chelation therapies for many of the afflictions alluded to in this article.
Hyman M. Schipper is a professor of neurology and medicine at McGill University and director of the Centre for Neurotranslational Research at the Lady Davis Institute for Medical Research, S.M.B.D. Jewish General Hospital, Montréal, QC.
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APRIL 2007 CANADIAN CHEMICAL NEWS 13
Gauging Material Efficiency
14 L’ACTUALITÉ CHIMIQUE CANADIENNE AVRIL 2007
John Andraos, MCIC
H
ow do you determine the material efficiency of a chemical reaction or a synthesis plan? This question has preoccupied chemists since Antoine Lavoisier’s discovery of the law of conservation of mass for chemical transformations in 1775. In the present context of the new field of green chemistry in which syntheses of chemicals and materials are to be conducted with the least impact on the environment, a quantitative description of material efficiency that can be applied to any synthesis plan in a standard way is important. Taking a wish list approach, one would like such a method to meet various criteria. For individual reactions it should take into account not only reaction yield to a given target, but also the use of solvents, excess reagents, and other work-up and purification materials. For synthesis plans, it should be robust in its application regardless of their complexity—that is, whether they are linear, convergent, or divergent. It should be possible to rank different plans to a common target according to various parameters in an unbiased way in order to weed out bad performing plans quickly and to understand why good plans are good. When these criteria are met, chemists can better focus their efforts toward synthesis optimization in a reliable way. Above all, we would like the method to be amenable to easyto-read visual representations so that features of reactions and synthesis plans may be seen quickly by inspection. This article briefly describes two novel visual diagrams to gauge material efficiency
that the reader can readily apply to their current work in chemistry. The first is a radial pentagon that depicts the global reaction mass efficiency of a chemical reaction and its dependence on reaction yield, atom economy, excess reagents, and all other materials used in the reaction, work-up, and purification phases. The second is a synthesis tree diagram that can be used to determine “green metric” parameters such as overall kernel atom economy and overall kernel reaction mass efficiency by a simple connect-the-dots approach. New parameters such as degree of convergence and degree of asymmetry may be determined from the shapes of such tree diagrams. Each of these parameters will be introduced and defined using illustrative examples. Both methods are rooted in balanced chemical equations as prescribed by Lavoisier’s conservation of mass law.
Individual chemical reactions If for a chemical reaction we designate the mass of target product as our output and the sum of the masses of all reactants as our input, then reaction mass efficiency (RME) is the ratio of output to input and the mass of waste produced and (w) is the difference between input and output. Reaction mass efficiency may be further decomposed into its four contributing factors each ranging in value between 0 and 1 as shown in Equation (1).1 For simplicity in calculations, all fractional quantities are written as decimal fractions instead of as percentages
⎛ 1 ⎞ RME = ( ε )( AE ) ⎜ ⎟ ( MRP ) ⎝ SF ⎠
(1)
where ε is the reaction yield (0 < ε < 1); AE is atom economy (0 < AE < 1); SF is the stoichiometric factor that takes into account the use of excess reagents (SF = 1 for stoichiometric reactions carried out with no excess reagents; SF >1, otherwise); MRP is the material recovery parameter that takes into account other materials used in the reaction and post-reaction phases (work-up and purification) such as solvents and washings for extractions (0 < MRP < 1); c, s, and ε are the masses of reaction catalyst, reaction solvent, and all other post-reaction materials respectively; and mP is the mass of the collected target product. Atom economy is given by the well known definition:
AE =
MWproduct
(2)
∑ MWreagents
and the stoichiometric factor, by definition, is given by:
SF = 1 +
∑ massexcess reagents
∑ massstoichimoetric reagents
=1+
∑ mass excess reagents
theoretical mass product
(3)
Each of the four factors in master equation (1) acts to attenuate RME with the MRP factor being the strongest attenuator since solvents normally account for the bulk mass of reaction materials used in a chemical reaction. The five parameters RME, AE, ε, 1/SF, and MRP may be displayed graphically in the form of a radial pentagon depicting a “materials usage footprint” so that one can recognize at once which of the four factors on the right hand-side of Equation 1 are contributing to an attenuation of RME. Each axis corresponding to one of the five parameters emanates from the centre and ranges in value between zero and one. The values of these parameters are depicted as dots and these are connected to form a
pentagonal figure. The ideal “green” situation is depicted by a regular pentagon of unit radius where each parameter is equal to one. The less “green” a reaction is, the more the resultant pentagon is distorted toward the centre. These diagrams may therefore be used to compare the RME performances of different classes of reactions so that a chemist can ascertain which reaction classes are inherently “green” and which are not by visual inspection. The degree of distortion of the radial pentagon from its regular ideal shape may be directly linked to parameters responsible for that distortion. These diagrams therefore inform chemists as to what to do if they wish to “green up” their experimental procedure, whether it is to reduce reaction solvent usage, cut down on unnecessary washes and extractions, avoid using excess reagents unless there is a chemical reason for doing so as in driving equilibria toward product, select lower mass reagents to effect improved atom economical performance, or optimize reaction yield by tweaking with such parameters as reaction time, reaction temperature, reaction pressure, or the use of catalysts. The following undergraduate laboratory procedure for the synthesis of diphenylmethanol using the Grignard methodology according to Scheme 1 is given as an illustrative example where the present analysis is employed. Figure 1 shows the corresponding resultant radial pentagon. Under conditions of using excess reagents (benzaldehyde is the limiting reagent) and committing all materials other than target product to waste, the overall RME for production of diphenylmethanol is 1.1 percent with a reaction yield of 80 percent and an atom economy of 56.9 percent. From this visual representation it is clear that the low overall RME is due to a modest AE of 60 percent, the use of 61 percent excess reagents (SF = 1.61), and a minimum MRP of about 4 percent. The best RME possible for synthesizing diphenylmethanol by this procedure is 28.2 percent if work-up and purification materials are recovered. When the material efficiencies of organic reactions are analyzed in a similar way according to their classification type, one can explore and discover important general trends that are useful in planning material efficient total syntheses of target molecules. A Microsoft Excel (Version 5.0 or higher) spreadsheet template form with embedded formulas2 has been developed that allows easy calculation of reaction mass efficiency and other “green” metrics, including raw material costs (RMC), for any chemical transformation. With this tool, students and seasoned practitioners may employ green metrics to evaluate the “greenness” of their experiment in a rigorous quantitative way and to determine the bottom line cost of carrying it out. It also gives user direction in assessing improvements experiment under various reclaiming and (or) recycling options with respect to materials usage and cost savings.
Synthesis plans The synthesis tree method2 is illustrated for the convergent synthesis of the alkaloid papaverine as shown by the traditional representation in Scheme 2. The corresponding synthesis tree diagram is shown in Figure 2. In this new representation input materials, isolated intermediates, and target product are represented as filled, open, and shaded dots respectively. The x-axis represents the number of reaction stages each with its designated reaction yield and the y-axis represents the number of input
APRIL 2007 CANADIAN CHEMICAL NEWS 15
Scheme 1. To a 25 mL round-bottomed flask charged with 0.4 g dry magnesium turnings is added dropwise a solution of 1.8 mL bromobenzene in 9 mL dry ether over 20 minutes. The reaction solution is gently refluxed for a further 20 minutes. A second solution of 1.5 mL benzaldehyde in 4 mL dry ether is added dropwise over a period of 20 minutes. After addition is complete the mixture is refluxed for 15 minutes then cooled. The reaction mixture is then poured over 10 g crushed ice followed by addition of 3 mL of 5 percent aqueous HCl solution. The ether layer is separated and washed successively with water (30 mL), saturated sodium bisulphite (NaHSO3) solution (30 mL), and again with water (30 mL). After drying with 5 g MgSO4, filtration, and evaporation of the solvent, the crude product is recrystallized from petroleum ether (100 mL) to afford 2.18 g of pure diphenylmethanol. Notes (i) Densities (g/mL): diethyl ether (0.708), petroleum ether (0.64), bromobenzene (1.495), benzaldehyde (1.046), water (1), 5 percent HCl solution (1.02), saturated NaHSO3 solution (1.345).
Scheme 2. Kindler-Peschke-Pal Synthesis of Papaverine (a) (MeO)2SO2 (90 percent); (b) H2/Pd (100 percent); (c) SOCl2/PhNMe2 (80 percent); (d) KCN (85 percent); (e) H2/Pd (79 percent); (f) HCl/H2O (100 percent); (g) (96 percent); (h) POCl3 (100 percent); (i) Pd (91 percent)
Figure 1. Radial pentagon representing RME values for the synthesis of diphenylmethanol using the Grignard methodology under various scenarios. See Scheme 1 for balanced chemical reaction. materials. Since this is a convergent plan, the first five stages involve parallel reactions, hence the total number of reactions in the plan (13) exceeds the number of stages (8). Linear plans have an equal number of reactions and stages. The input dots are entered one unit apart in the y-direction and the ordinates of the intermediate dots are the centroids of the ordinates of the immediately preceding input dots. For a target scale in moles of the product, it is possible to calculate the mass of any input reactant by following the connections between that input dot and the target dot in the diagram. This is done by working backwards remembering that going from right to left represents amplification in reaction scale. For example, for 1 mole of papaverine the masses of intermediates I5* and I5 required are MW15* (1 / ε6ε7ε8 ) and MW15 (1/ ε6ε7ε8 ) grams, respectively. The mass of dimethylsulfate (DMS) required is MWDMS 0.5 ⎡⎣(1 / ε1ε2ε3ε 4ε5ε6ε7ε8 ) + (1 / ε1ε2ε3ε 4ε5*ε6ε7ε8 ) ⎤⎦ g r a m s . The total mass of hydrogen required for the entire synthesis is MWH2 ⎡⎣(1 / ε2ε3ε 4ε5ε6ε7ε8 ) + (1 / ε2ε3ε 4ε5*ε6ε7ε8 ) + 2 (1 / ε5ε6ε7ε8 ) ⎤⎦
16 L’ACTUALITÉ CHIMIQUE CANADIENNE AVRIL 2007
grams. The kernel reaction mass efficiency for this plan is obtained from a reduced form of Equation (1) using the masses of input materials determined by the above procedure, where it is assumed that no excess reagents are used and solvents and work-up and purification materials are recovered. In effect the kernel RME for each reaction is the product of AE and the reaction yield. This gives the best possible RME performance corresponding to the chemistry in the plan. Such a parameter is a truer measure of material efficiency than overall yield. Other parameters such as degree of convergence, degree of asymmetry, and molecular weight building-up index may also be easily deduced from the tree diagram (see reference 3 for details). One can see that tree diagrams give a compact visualization of synthesis plans from which important quantitative parameters may be easily calculated. It is also an excellent method of proofreading plans reported in the literature and of bookkeeping the correct balancing of all chemical reactions. Table 1 summarizes the “green metrics” results of this synthesis plan and others for this target molecule from different starting materials (see Scheme 3). Optimization is achieved by an iterative process until “good” attributes for all metrics occur in the same plan. One can see that the Kindler-Peschke-Pal plan is the most satisfactory plan since it has the highest overall kernel RME, the second-highest overall atom economy, the least number of reaction stages, the highest (most negative) building-up parameter,4 the highest degree of convergence, the least asymmetry, and most importantly, is the least costly in terms of input materials.
Acknowledgements Parts of this article were presented in a talk given at the International Symposium on Green Chemical Processes for Pharmaceuticals and Fine Chemicals at McGill University, October 20–22, 2006.
Figure 2. Synthesis tree for Kindler-Peschke-Pal synthesis of papaverine (see Scheme 2)
Scheme 3. Various documented synthesis plans for papaverine from different starting materials
Table 1. Summary of reaction metrics and synthesis tree parameters for papaverine synthesis plans Pictet-Gams
Decker-Wahl
Redel-Bouteville
Kindler-Peschke-Pal
Dean
Kernel reaction metrics AE
0.136
0.197
0.317
0.274
0.199
RME
0.0052
0.0275
0.0404
0.151
0.0796
εpseudo-overall
0.038
0.138
0.127
0.550
0.400
Number of reaction inputs, I
18
20
11
15
12
Number of reaction steps, M
11
12
8
13
10
Number of reaction stages, N
8
9
8
8
8
-223.18
-83.10
-29.96
-280.23
-212.89
29.04
4.72
8.17
0.45
22.05
μm1(g per mole per reaction stage) RMCa (CAD$ per gram)
Tree parameters Degree of convergence, δ
0.443
0.425
0.359
0.450
0.392
Asymmetry, β
0.813
0.861
0.746
0.604
0.630
References John Andraos, MCIC, is a lecturer and course director in the department
1. John Andraos, J. Org. Process Res. Develop. 9 (2005), 149. 2. John Andraos, M. Sayed, J. Chem. Educ. 84 (2007), in press. 3. John Andraos, J. Org. Process Res. Develop. 10 (2006), 212. 4. Synthesis plans beginning from low molecular weight starting materials that react to produce progressively heavier intermediates along the way until the target product is reached have large negative molecular weight first moments.
of chemistry at York University. His research is in the areas of quantitative analysis of synthesis plans, reaction optimization, green chemistry, and kinetic analysis of homogeneous and heterogeneous systems. In 2000, he founded CareerChem, which is an educational and career mentoring Web site for chemists (www.careerchem. com/MainFrame.html). He has also given career workshops at national CSC meetings for those seeking academic positions.
APRIL 2007 CANADIAN CHEMICAL NEWS 17
THE CSC ACCREDITATION PROGRAM John M. McIntosh, FCIC
M
ore than 20 years ago, at the urging of Dennis Tuck, FCIC, of the University of Windsor, the Canadian Society for Chemistry initiated a program to ensure that undergraduate chemistry program requirements would be comparable across Canada. This was started in response to suggestions by employer groups who wanted assurances that new graduates could be counted on to have had exposure to the (then) four basic sub-disciplines of analytical, inorganic, organic, and physical chemistry. The parameters used to achieve this end allowed flexibility in course arrangement and content, but required a “finished product” that had certain fundamental skills on which employers could count—including experience with major instrumental techniques common in chemistry laboratories, and exposure to a reasonable variety of advanced topics in chemistry. This process of accreditation was, and still is, unique to the Canadian system. The American Chemical Society, through its Committee on Professional Training, provides a method for certification of students but not accreditation of programs. In the years since its inception, a number of developments have occurred that make this accreditation program increasingly important. The question of professional status for chemists has become of major importance, particularly in the area of environmental remediation. As this is a provincial issue, several provinces, led by Quebec, have formed associations to lead the movement toward licensure and to
18 L’ACTUALITÉ CHIMIQUE CANADIENNE AVRIL 2007
provide a governing body for professional chemists. The Ordre des chimistes du Québec (OCQ) was the first one formed and, to date, has been the most successful in achieving professional status for practising chemists in that province. In order to practise the science of chemistry in Quebec, one must be a member of the OCQ. Admittance to that organization is based (at least in part) on graduation from a program that has demonstrated that it meets their requirements for accreditation. Currently, two other provinces have established similar associations. Ontario has the Association of the Chemical Professions of Ontario (ACPO) and Alberta has the Association of the Chemical Professions of Alberta (ACPA). Legislation required to provide the licensure has not been passed. In addition, similar associations are developing in the Maritimes and BC. Eligibility for membership in these organizations is also based on graduation from a program that fulfils their requirements. Since these associations are provincial in scope, but chemistry graduates can move from province to province, a national system for providing assessment of chemistry programs became a necessity. The accreditation program provided by the CSC is filling this role and graduates from accredited programs have qualifications that provide automatic entry into these associations. Since the inception of the program, the science of chemistry has changed enormously. Fragmentation of the basic sub-disciplines into more tightly defined areas has become common. Terms like
“bio-organic,” “nano,” “materials,” etc. are now major players in the field. In 2000, a motion was passed by the CSC Board to expand the required sub-disciplines to five with the inclusion of biochemistry. This requirement became mandatory in 2005. Many arguments have been received by the Society both pro and against the addition of this requirement. Opinions have been expressed that other areas like materials chemistry are just as important (especially to those on the non-biological end of the chemistry spectrum) and if biochemistry is to be included, so should these other areas. It must be noted that the accreditation program focuses on undergraduate programs only and does not legislate against the inclusion of any sub-discipline in the program. The CSC continues to support the current requirements in the belief that a graduate chemist should be able to interact with workers in the biological fields. Currently, the course work requirements for accreditation are a minimum of two semesters of study in at least three of the five sub-disciplines of analytical, physical, inorganic and organic chemistry, and biochemistry (possibly as a bio-organic chemistry course), but with a minimum of at least a one-semester course in each of these five areas. In addition, the requirements include two semesters of calculus-based physics, two semesters of calculus, plus one semester of an additional mathematics or computer science. There must be a total of 1,000 contact hours of chemistry instruction, at least 400 of which should be laboratory hours. Beyond the required courses, the departments are free to offer whatever types of courses or groups of courses they feel appropriate to fill the required hours. Initially, there were requirements regarding library journal holdings but with the advent of electronic access to journals, in practice this requirement, although still a formal part of the accreditation guidelines, has become largely obsolete. Programs must also demonstrate the presence of educational components (but not necessarily courses) that introduce students to topics considered important by many employers, such as professional ethics and responsibility, communication skills, and teamwork. It is important to note that it is programs, not departments, that are accredited. Thus, any department may have several programs, but only some of these might meet the requirements for accreditation. The accreditation program requires an application from a
department. The application form and the full “CSC Guidelines for Accreditation” as well as the membership of the current accreditation committee can be found at the CSC Web site (www.chemistry.ca) under “Accreditation.” After ensuring that the program meets the basic requirements, an extensive document detailing many aspects of the department must be filed with the CSC Accreditation Committee. This is followed by a site visit by two or three individuals experienced in the operation of Canadian chemistry departments to examine the department and programs in detail. The site visit normally entails interviews with faculty, students, senior university administrators, and librarians. Depending on the size of the department and the number of programs being considered, a site visit can last one or two days. A report is then generated by the site visit team (SVT) and circulated to the Accreditation Committee. It is important to note that the SVT attempts to write the report in a manner that is supportive of the department’s needs to provide and improve its programs of instruction. If the CSC Accreditation Committee finds that the program meets the required standard, the committee recommends its accreditation to the CSC board of directors. The status is granted for a five-year period (first cycle), at which point another application for extension of the status for a second five-year period (second cycle) is required. If no substantive changes have been made, no site visit is required at this point. After the expiration of this time, the site visit process must be repeated. At present, there are 36 universities with 128 accredited programs in Canada. The full list of universities and accredited programs can be found on the CSC Web site. A very recent development is the request by overseas departments to be accredited under our system. The first of these was the University of Kuwait, and there are currently a number of applications arriving from other universities in the same area of the world. As the CSC is the only society to provide this service, we are being approached by schools that want to ensure that their programs are comparable to the best—the Canadian ones!
John M. McIntosh, FCIC, is chair of the CSC Accreditation Committee and emeritus professor of organic chemistry at the
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APRIL 2007 CANADIAN CHEMICAL NEWS 19
RECOGNITION RECONNAISSANCE
NSERC appoints Jillian Buriak, MCIC. The Natural Sciences and Engineering Research Council of Canada (NSERC) has appointed Jillian Buriak, MCIC, as a member of the Council. “Buriak has a strong understanding of university research and the sciences that will benefit the Council,” said Honourable Maxime Bernier, Minister of Industry. “Her knowledge and experience will provide valuable contributions to NSERC as it continues to promote and support research in universities, government, and the private sector.” Buriak is currently professor of chemistry and holds a Canada Research Chair position in Inorganic and Nanoscale Materials with the University of Alberta. She is also the senior research officer and group leader with the National Institute for Nanotechnology. She has earned several awards throughout her career, including the 2006 Faculty of Science Research Prize from the University of Alberta, the Martha Cook Piper Research Prize in 2005 and the American Chemical Society’s Pure Chemistry Award in 2003. In 2003, she was recognized as a member of Canada’s Top 40 Under 40, a program that honours Canadians who have reached a significant level of success before the age of 40.
Suzanne Fortier, FCIC, president of the Natural Sciences and Engineering Research Council of Canada (NSERC), announced that a team of researchers based at the University of Manitoba (U of M), along with their collaborators at MDS Sciex and Agriculture and Agri-Food Canada, have won the third annual Brockhouse Canada Prize for Interdisciplinary Research in Science and Engineering. The prize includes $250,000 in funding for future research activities.
20 L’ACTUALITÉ CHIMIQUE CANADIENNE AVRIL 2007
NSERC president Suzanne Fortier, FCIC (front row, second from right), and U of M president Emöke Szathmàry (front row left) join the winners of this year’s Brockhouse Prize. Winners include Harry Duckworth, MCIC (top row left), Hélène Perreault, MCIC (top row, third from left), and Kenneth Standing, MCIC (front row, centre). Members of the team have spent more than a decade refining proteomics techniques that can be applied to a wide range of problems in medicine and biology. One of their greatest successes came in 2003 when team members, led by Kenneth Standing, MCIC, were the first worldwide to determine the structure of the protein component of the Severe Acute Respiratory Syndrome (SARS) virus. Along the way, the team has also developed patented improvements to their key tool, the mass spectrometer. While genes provide a blueprint, proteins actually carry out the cell’s work. Because proteins are so numerous, analysing them is a far more complex process than sequencing a genome. Along with Standing, U of M chemists Harry Duckworth, MCIC, and Hélène Perreault, MCIC, are among those being honoured with the Brockhouse Prize. “This year’s winners form a ‘virtuous circle’ where academic researchers and private sector engineers collaborate to develop the leading-edge equipment needed for new discoveries,” said Fortier. “I’m especially impressed to see the team combine such a wide variety of disciplines, including physics, engineering, chemistry, and cell biology.” U of M president and vice-chancellor, Emöke Szathmáry, said the winning team is a perfect example of the level of collaboration and partnership vital to scientific research in the 21st century. Named after Bertram Brockhouse, the Canadian Prairie-born Nobel laureate, the prize honours teams of researchers that combine different disciplines to produce
achievements of international scientific or engineering significance. Over the last ten years, NSERC has invested more than $6 billion in basic research, university-industry projects, and the training of Canada’s next generation of scientists and engineers.
Basell announced that Michael Mulrooney has been appointed president of Basell Polyolefins North America. In his new role, Mulrooney is responsible for Basell’s polypropylene operations in Canada, the U.S., and Mexico.
Ian Smith, FCIC,was awarded an honorary professorship in the Polish Academy of Sciences, at their Institute of Nuclear Physics, Krakow. This award is given in recognition of contributions to Polish science and the commercialization of Polish technology.
Dalhousie University is pleased to announce that it has entered into a licence agreement with Strem Chemicals Inc. of Newburyport, MA, for the production, marketing, and selling for research purposes of six novel catalysts developed by Mark Stradiotto, MCIC. His catalysts will be useful in a wide range of applications and will be listed in Strem’s catalogue and sold for research purposes. Dalhousie will retain the rights to exclusively license any of the chemicals for commerical purposes.
RECOGNITION RECONNAISSANCE
Alison Thompson, MCIC, has been awarded the Dalhousie Faculty of Science Killam Prize for 2006–2007 for outstanding research performance as a young faculty member.
Donald F. Weaver, FCIC, of Dalhousie University, was presented with the Professional of Distinction 2006 award. This award is presented by the Discovery Centre in its Discovery Awards for Science and Technology series.
Michael Wilson, MCIC, president and CEO of Agrium Inc., was elected vice-chair of the board of directors of the International Plant Nutrition Institute (IPNI) for a two-year term. He will serve as a member of the IPNI Executive Committee. IPNI is a new, not-for-profit, scientific organization dedicated to responsible management of plant nutrients—N, P, K, secondary nutrients, and micronutrients—for the benefit of the human family. IPNI provides a unified, scientific voice for the world’s fertilizer industry; independent of the industry, but scientifically credible and recognized by governments, academia, NGOs, the public, and the industry. Agrium Inc., PotashCorp, Saskferco, and Spur Ventures Inc. are among the founding members of IPNI.
2006 CIC Society Silver Medalists The CIC is proud to announce the 2006 Silver Medal winners. The medals are awarded to undergraduate students on behalf of each society.
Les médaillés d’argent 2006 des sociétés de l’ICC
L’ICC est fière d’annoncer les gagnants des médailles d’argent 2006. Chaque société octroie ces médailles à des étudiantes et des étudiants de premier cycle.
CSC Silver Medal Winners The CSC encourages undergraduate students in chemistry and related subjects by offering an award to the student with the highest marks, in his or her penultimate year of studies at each chemistry and/or biochemistry department in Canada. The recipients of the CSC Silver Medal receive an engraved medal and a certificate of merit. The society offers its congratulations to those students who received the CSC Silver Medal.
Gagnants de la médaille d’argent de la SCC La SCC souligne les efforts des étudiants de premier cycle en chimie ou autres matières connexes en décernant un prix à l’étudiante ou l’étudiant qui obtient les meilleurs résultats scolaires au cours de son avant-dernière année d’études dans un programme conduisant à l’obtention d’un diplôme en chimie ou en biochimie. Les récipiendaires des médailles d’argent reçoivent une médaille gravée accompagnée d’un certificat de mérite. La Société tient à féliciter les étudiantes et les étudiants qui ont mérité cette médaille.
In Memoriam The CIC extends its condolences to the families of: J. Bumbulis, FCIC Lars Firing, MCIC W. N. Hall, FCIC Charles MacDonald, MCIC Nicholas Sturges, MCIC H. G. Winnett, MCIC
Geoff Rayner-Canham, FCIC (right), and head of science, Lois Bateman (left), present the CSC silver medal to Tonia Churchill, ACIC, of Sir Wilfred Grenfell College.
RECOGNITION RECONNAISSANCE
Bishop’s University
Queen’s University
University of Calgary
• Chemistry/Biochemistry Starr Dostie
• Chemistry Samantha Kwok
• Chemistry Dustin William H. Banham
Brock University
Ryerson University
University of Guelph
• Chemistry Fred Barrett
• Chemistry Steven Wong
Cape Breton University
Simon Fraser University
• Applied pharmaceutical chemistry Lee Salsberg • Chemistry Michelle Paquette
• Bachelor of Technology (Chemical Science) Jennifer Lynn MacDonald
• Chemistry Rince Wong
University of Manitoba
Dalhousie University • Chemistry Amy Trottier
McGill University • Biochemistry Kevin Eric Shopsowitz • Chemistry Tara Irene Yacovitch
McMaster University • Biochemistry Lauren Sule • Chemistry Julie Lebert
Sir Wilfred Grenfell College • Environmental chemistry Tonia Churchill
Thompson Rivers University • Chemistry Bryan Karolat Nicole Ilic
Trent University • Chemistry Heather Ritter
Université de Moncton
Mount Allison University
• Biochimie Renée St-Onge • Chimie Luc-Henri Bourgoin
• Chemistry Sarah Dobrowolski
Université de Montréal • Chimie Chantal Durette
CSChE Chemical Engineering Local Section Scholarships The Canadian Society for Chemical Engineering offers two CSChE Chemical Engineering Local Section Scholarships annually to undergraduate students in chemical engineering at a Canadian university. Sponsored by the Edmonton CSChE, Sarnia CIC, and London CIC Local Sections.
Deadline: April 30, 2007 For details visit www.chemeng.ca/ lsscholarships.
22 L’ACTUALITÉ CHIMIQUE CANADIENNE AVRIL 2007
Université du Québec à Trois-Rivières • Chimie et biochimie Caroline Bigras
Université Laval • Chimie Guillaume Bélanger-Chabot
University College of the Fraser Valley • Chemistry Christine McLoughlin
University of Alberta • Chemistry Nicole E. Oro
University of British Columbia • Chemistry Michael Stanley Lynch
• Biochemistry William Guest • Biotechnology Ainsley Winter • Chemistry Matthew William Kotyk
University of New Brunswick • Chemistry Jeffrey McDowell
University of Regina • Chemistry Ywomo Daniel Yowin
University of Saskatchewan • Chemistry Sara Bonderoff
University of Toronto • Chemistry Derek Tsang
University of Toronto – Mississauga • Forensic science – chemistry specialist Taehan Kim
University of Toronto – Scarborough • Chemistry John Norman Westgate
University of Victoria • Chemistry Devin Mahnke
University of Windsor • Biochemistry Catherine Cheng • Chemistry Meghan Doster
York University • Chemistry Katarzyna Jerzak
Officer Cadet Erin Elizabeth McEachern, ACIC, receives her silver medal at RMC.
CSChE Silver Medal Winners In addition to the medal and certificate of merit offered by all the societies, the CSChE awards an additional prize of $50 and a one-year membership to the CSChE. Winners have achieved top marks in their penultimate year of a chemical engineering program. The society wishes to congratulate those students who received the CSChE Silver Medal.
New with YOU?
RECOGNITION RECONNAISSANCE
What’s
Gagnants de la médaille d’argent de la SCGCh La SCGCh décerne comme toutes les autres sociétés des médailles et des certificats de mérite. Cependant, elle désire accorder un prix additionnel de 50 $ et une adhésion d’un an à la SCGCh aux étudiantes et étudiants qui auront obtenu les meilleurs résultats scolaires au cours de leur avant-dernière année d’études dans un programme de génie chimique. La société désire féliciter les étudiantes et les étudiants qui ont mérité la médaille d’argent de la SCGCh.
Vicky Whiffen
McMaster University Andrew Kennedy
Royal Military College of Canada Erin Elizabeth McEachern
Ryerson University Noel Jacob
Université de Sherbrooke Pierre-Luc Gagnon
University of Alberta Shanshan Liu
University of Calgary Leslie Patricia Wilkins
University of New Brunswick Ryan Ward
University of Ottawa
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University of Saskatchewan Stefan Sigurdson
University of Toronto Joshua Harris
ACCN
Dalhousie University
from your company, classroom, or laboratory to
editorial@accn.ca. APRIL 2007 CANADIAN CHEMICAL NEWS 23
RECOGNITION RECONNAISSANCE
SNC-LAVALIN Plant Design Competition The Canadian Society for Chemical Engineering offers the SNC-LAVALIN Undergraduate Plant Design Competition for students enrolled in undergraduate chemical engineering
CSCT president, Joffre Berry, MCIC, with BCIT Chemical Science Technology award winner, Mark Roberts (right)
CSCT Silver Medal Winners The CSCT extends congratulations to those students attending community college or cégep who received the society’s medal. The students listed have achieved top marks in their final year of chemical, biochemical, or chemical engineering technology program.
programs at Canadian Universities. Individuals and groups of undergraduate students registered in chemical
Gagnants de la médaille d’argent de la SCTC
are eligible.
La SCTC tient à féliciter les étudiantes et étudiants qui se sont vu décerner la médaille d’argent de la SCTC. Ces étudiants des cégeps ou des collèges communautaires ont obtenu les meilleurs résultats scolaires au cours de la dernière année de leur programme de technologie chimique, biochimique ou de génie chimique.
Deadline: May 15, 2007
British Columbia Institute of Technology
For more information go to
• Chemical science technology Mark Roberts
engineering programs in Canadian universities during the academic year
Centennial College
• Chemical engineering technology – environmental Megan Clarke • Environmental technician Elaine Barton
• Biological, chemical, environmental Quanxi Nong
New Brunswick Community College
chimique offre le concours de concep-
Durham College
• Chemical technology Denise Duplessis
tion d’installation SNC-LAVALIN aux
• Biotechnology Laura Bush • Chemical engineering technology Allan Nixon • Environmental technology Candice Quibell • Pharmaceutical and food science technology Tammy Deshevy
www.chemeng.ca/snclavalin
La Société canadienne de génie
étudiants de premier cycle inscrits à des programmes de génie chimique dans des universités canadiennes. Les étudiants et groupes d’étudiants de premier cycle inscrits à des programmes de génie chimique dans des universités canadiennes pendant
Seneca College • Chemical engineering technology Amanda Jameer • Chemical laboratory technology – pharmaceutical Li Tan
Southern Alberta Institute of Technology
Humber College
• Chemical technology Rocky Martin
• Chemical engineering technology Luzi Gandhi
St. Clair College
renseignements visitez
Mohawk College
• Chemical technology Sinisa Djurdjevic
www.chemeng.ca/snclavalin
• Chemical engineering technology Natalija Mirilovic
l’année universitaire sont admissibles.
Date limite : le 15 mai 2007 Pour de plus amples
24 L’ACTUALITÉ CHIMIQUE CANADIENNE AVRIL 2007
RECOGNITION RECONNAISSANCE
CNC-IUPAC Travel Awards for 2008 Bourses de voyage du CNC-UICPA pour 2008 The Canadian National Committee for IUPAC (CNC-IUPAC) established a program of Travel Awards for young Canadian scientists in 1982. These awards are financed jointly by the Canadian Society for Chemistry’s Gendron Fund and by CNC-IUPAC’s Company Associates: Merck Frosst, Boehringer Ingelheim, and Bruker BioSpin. The purpose of these awards is to help young Canadian scientists and engineers, who should be within ten years of gaining their PhDs, present a paper at an IUPAC-sponsored conference outside Canada and the U.S. Deadline for receipt of applications: October 15, 2007. Details of the applications procedures can be found at www.cnc-iupac.ca.
Le Comité national canadien de l’Union internationale de chimie pure et appliquée (CNC-UICPA) remet des bourses de voyage aux jeunes scientifiques canadiens depuis 1982. Ces bourses sont subventionnées par le Fonds Gendron (administré par la Société canadienne de chimie) et par les compagnies associées au CNC-UICPA : Merck Frosst, Boehringer Ingelheim et Bruker BioSpin. L’objectif de ces bourses est de venir en aide aux jeunes scientifiques et ingénieurs canadiens qui sont à moins de 10 ans d’obtentir leur doctorat afin de leur permettre de présenter leurs travaux lors d’un congrès commandité par l’UICPA à l’extérieur du Canada et des États-Unis. Date limite pour postuler : le 15 octobre 2007. Renseignements supplémentaires : www.cnc-iupac.ca.
macromolecular science. His groups work has led to the development of unprecedented parallels between P=C and C=C bonds in polymer science and includes the synthesis of the first addition polymers of P=C bonds.
Ulrich Fekl received his PhD (summa cum laude) in 2000 from the University of Erlangen-Nürnberg, Germany under the supervision of Rudi van Eldik, for research on mechanisms of inorganic and organometallic reactions. Studies included conventional and high-pressure conditions. He then moved to the University of Washington in Seattle, WA, to work with Karen Goldberg on novel platinum(IV) and platinum(II) systems for alkane C-H bond activation. He held a DAAD post-doctoral fellowship in 2000–2001. In 2003, he took up a faculty position at the University of Toronto. His current research interests include the synthesis of transition metal Lewis-acids to catalyze organic reactions, synthesis of cage-type architectures, as well as reactions at coordinated ligands. Fekl received the CNC/IUPAC Travel Award for 2007, which he will use to attend the 14th IUPAC Symposium on Organometallic Chemistry in Nara, Japan. Fekl’s research concentrates on novel organometallic and inorganic reactions.
Derek Gates, MCIC, is an associate professor of chemistry at The University of British Columbia (UBC). He received his BSc from Dalhousie in 1993 and his PhD from the University of Toronto in 1997 under the direction of Ian Manners, FCIC. Gates then moved to the University of North Carolina at Chapel Hill where he was an NSERC post-doctoral fellow with M. Brookhart. He began his independent career as an assistant professor at UBC in 1999. His research interests span the areas of synthetic main group and macromolecular chemistry. A major theme involves establishing analogies between phosphorus and carbon in polymer science. For instance, his group has established the first addition polymerization reactions for P=C bonds and they have developed conjugated phosphorus analogues of poly(p-phenylenevinylene). This CNC-IUPAC Travel Award will support his participation in the 17th International Conference on Phosphorus Chemistry (ICPC) in Xiamen, China (April 15–21, 2007). Gates’ research interests lie at the interface between main group chemistry and
Mark MacLachlan, MCIC, was born in Faro, Yukon, and received his BSc from The University of British Columbia in 1995. He obtained his PhD at the University of Toronto working under the joint supervision of Ian Manners, FCIC, and Geoffrey Ozin, FCIC, in inorganic materials chemistry. After two years at M.I.T. as an NSERC post-doctoral fellow with Timothy Swager, MacLachlan returned to UBC as an assistant professor in 2001. His research program in inorganic supramolecular chemistry is focused on the development of shape-persistent macrocyclic ligands and their coordination chemistry, with the goal of assembling them into nanotubes and frameworks. He is grateful to receive the CNC-IUPAC travel award that will enable him to attend and present an invited lecture at the 12th IUPAC International Symposium on
APRIL 2007 CANADIAN CHEMICAL NEWS 25
RECOGNITION RECONNAISSANCE
Macromolecular Complexes held in Fukuoka, Japan in August 2007. MacLachlan will present a paper on his group’s recent investigations of synthesis and organization of multimetallic macrocycles.
EVENTS ÉVÉNEMENTS
Canada Conferences May 22–25, 2007. First Georgian Bay International Conference on Bioinorganic Chemistry (CanBIC), Parry Sound, ON, www.uwo.ca/chem/canbic May 26–30, 2007. 90th Canadian Chemistry Conference and Exhibition, Winnipeg, MB, www.csc2007.ca May 29–June 1, 2007. International Chemical Recovery Conference “Efficiency and Energy Management,” Québec, QC, 514-392-6964 July 8–12, 2007. CHEMRAWN-XVII and ICCDU-IX Conference on Greenhouse Gases: Mitigation and Utilization, Kingston, ON October 28–31, 2007. 57th Canadian Chemical Engineering Conference, Edmonton, AB, www.csche2007.ca
Andreea R. Schmitzer, MCIC, obtained her PhD at Université Paul Sabatier in France under the supervision of Isabelle Rico-Lattes and was a Canadian National Cancer Institute post-doctoral fellow in the group of Joelle Pelletier at the Université de Montréal. She is currently an assistant professor in the department of chemistry at the Université de Montréal. She is engaged in a multidisciplinary research effort to uncover new chemical and biochemical approaches for the design of functional molecular, supramolecular, and complex self-organized systems. Her endeavors span disciplines ranging from synthetic organic, bioorganic, and physical organic chemistry to nanotechnology, biophysics, enzymology, and molecular biology. The driving force for research on interlocked molecules in her group is perhaps not the synthetic challenge but the interesting properties and potential applications of the molecules themselves. With the support of the CNC-IUPAC Travel Award, Schmitzer will attend the 41st IUPAC World Chemistry Congress in Turin, Italy from August 5–11, 2007.
May 24–28, 2008. 91st Canadian Chemistry Conference and Exhibition, Edmonton, AB, www.csc2008.ca October 19–22, 2008. 58th Canadian Chemical Engineering Conference, Ottawa, ON, www.csche2008.ca August 23–27, 2009. 8th World Congress of Chemical Engineering and 59th Canadian Chemical Engineering Conference, Montréal, QC, www.wcce8.org
Student Conferences May 4–6 2007. Western Undergraduate Student Chemistry Conference, University of Saskatchewan, Saskatoon, SK, mam598@mail.us ask.ca May 2007. 32nd CIC-APICS Undergraduate Chemistry Conference (ChemCon2007), Acadia University, Wolfville, NS, 062548m@acadian.ca October 26, 2007. Colloque annuel des étudiants et étudiantes de 1er cycle en chimie, Université de Sherbrooke, Sherbrooke, QC, Pierre.Harvey@usherbrooke.ca
U.S. and Overseas May 29–June 10 2007. NSF Pan-American Advanced Studies on Sustainability and Green Chemistry 2007, Mexico City, Mexico June 21–23, 2007. Chemtech 2007, Institute of Chemistry, Ceylon, Colombo, Sri Lanka, info@ichemc.com, www.ichemc.com June 25–28, 2007. 11th Annual Green Chemistry and Engineering Conference, Washington, D C. July 1–5, 2007. 3rd International Conference on Green and Sustainable Chemistry, Delft, The Netherlands July 22–26, 2007. 23rd Annual Meeting of the International Society of Chemical Ecology, Jena, Germany, www.chemecol.org/meetings/meetings.htm
AC C N
View ACCN back issues at
www.accn.ca
August 4–12, 2007. IUPAC 44th General Assembly, Torino, Italy, www.iupac.org/symposia/ conferences/ga07 August 5–11, 2007. IUPAC 41st Congress, “Chemistry Protecting Health, Natural Environment and Cultural Heritage,” Torino, Italy,www.iupac2007.org. September 16–21 2007. 6th European Congress of Chemical Engineering (ECCE-6) Copenhagen, Denmark, www.ecce6.kt.dtu.dk
26 L’ACTUALITÉ CHIMIQUE CANADIENNE AVRIL 2007
CHEMFUSION
… continued from p. 8
antioxidants. The superstars may not work as well without the right supporting cast. After all, most of the over 200 studies that have demonstrated the benefits of antioxidant consumption were based on fruits and vegetables rather than supplement intake. These foods have numerous components other than the famous vitamins that can contribute to antioxidant activity. A Cornell University study, for example, clearly showed that Vitamin C as an integral part of fruit juices was more effective at reducing the formation of carcinogenic nitrosamines in the body than when taken as a supplement. It seems that chlorogenic acid in the juice boosts Vitamin C activity! So what are we to do? There is no argument that we should be eating at least five servings of a variety of fruits and vegetables every day. Only about ten percent of North Americans eat the suggested five servings a day, and for various social and economic reasons, no amount of cajoling is going to dramatically change this. Furthermore, even diets rich in fruits and vegetables may not include the optimal amount of Vitamin E. So although many claims about antioxidants may be exaggerated, current research supports daily supplementation with 200 mg Vitamin C and 200 to 400 IU of Vitamin E. While it is unrealistic to expect these nutrients to compensate for the effects of an unhealthy lifestyle, their benefits outweigh any risk. One day research might prove that other antioxidants may also be appropriate as supplements. Perhaps even BHT to slow down aging which, after all, is just a slow rotting process. But for now, anyone for some Cheerios®? (Check the label. They’re preserved with BHT!)
Popular science writer, Joe Schwarcz, MCIC, is the director of McGill University’s Office for Science and Society. He hosts the Dr. Joe Show on Montréal’s radio station CJAD. The broadcast is available on the Web at www.CJAD.com. You can contact him at joe.schwarcz@mcgill.ca.
COLLEGE CHEMISTRY CANADA LA CHIMIE COLLÉGIALE AU CANADA The 34th conference of College Chemistry Canada will be held jointly with the Chemical Society of Canada, May 26–31, 2007, in Winnipeg, MB. The host college for C 3 members will be the Collège universitaire de Saint-Btoniface, who will organize the social and special events. For more information go to: http://sp.cusb.ca/cusb/c3conference/index.html.
APRIL 2007 CANADIAN CHEMICAL NEWS 27
CAREERS CARRIÈRES
The Department of Chemistry
University of New Brunswick Applications are invited for an appointment (tenure-track) as a laboratory instructor to commence August 1, 2007, pending budgetary approval. Qualifications required include an M.Sc. or higher in any area of organic chemistry. Experience in either teaching or research after the Ph.D. is considered an asset. Candidates should have a demonstrated commitment to effective teaching at the undergraduate level. The Department is particularly interested in candidates who are committed to the design and use of multimedia-based courseware for teaching in classroom, laboratory and web-based settings. Candidates should submit a curriculum vitae, a list of publications and a statement of teaching philosophy which includes their teaching goals by May 18, 2007 to:
Chair Department of Chemistry University of New Brunswick P.O. Box 45222 Fredericton, NB Canada E3B 6E2 Candidates should arrange for three (3) letters of reference to be sent directly to the Chair. Review of applications will begin immediately after the closing date. All qualified candidates are encouraged to apply; however, Canadians and permanent residents will be given priority. Applicants should indicate current citizenship status. THE UNIVERSITY OF NEW BRUNSWICK IS COMMITTED TO THE PRINCIPLE OF EMPLOYMENT EQUITY.
28 L’ACTUALITÉ CHIMIQUE CANADIENNE AVRIL 2007
University of Utah As part of the Utah Science, Technology and Research (USTAR) Initiative for economic development in the State of Utah in the area of fossil energy, The University of Utah seeks an outstanding senior individual for a tenured faculty position at the rank of Professor or Associate Professor who demonstrates expertise and extensive experience in the area of oil sands/oil shale research and development. The successful candidate will be expected to be a national leader in his/her area and bring a significant externally funded research program to the University of Utah and have a demonstrated record in leadership, publication and teaching excellence. Applicants must have an earned Ph.D. in chemical engineering, or a closely related field. Before hiring, the selected candidate must provide proof of U.S. citizenship or authorization to work in the U.S. Interested persons should send a cover letter, vitae, detailed statement of research and teaching interests and at least three reference contacts to: Search Committee Department of Chemical Engineering University of Utah 50 S Central Campus Dr. Rm 3290 Salt Lake City, UT 84112 Applications will be accepted until the position is filled. The position will be available as of July 1, 2007. Applicants should reference this announcement in their cover letters.
The University of Utah, an Equal Opportunity, Affirmative Action Employer, encourages applications from women and minorities, and provides reasonable accommodation to the known disabilities of applicants and employees.
APRIL 2007 CANADIAN CHEMICAL NEWS 29
30 L’ACTUALITÉ CHIMIQUE CANADIENNE AVRIL 2007
APRIL 2007 CANADIAN CHEMICAL NEWS 31
90th CANADIAN CHEMISTRY CONFERENCE AND EXHIBITION
Undergraduate Student Poster Competition Are you working on a research project and want to share your results? Do you have a paper to present at a Canadian Society for Chemistry (CSC) Undergraduate Student Chemistry Conference and would like to present it again in poster format? Are you interested in presenting a poster for the first time? Here is an opportunity to show your peers and chemical professionals what you can do. The CSCâ&#x20AC;&#x2122;s 90th Canadian Chemistry Conference and Exhibition will be taking place May 26â&#x20AC;&#x201C;30 in Winnipeg, MB. We invite you to participate in the undergraduate poster competition that will be organized during this event. Posters will be accepted in the general areas of analytical, inorganic, organic and physical chemistry, as well as in biochemistry. Two awards will be given in each area ($150 for 1st prize and $50 for 2nd prize). The amount may increase depending on the number of participants. Some travel assistance is available to undergraduate students attending the conference.
Eligibility This competition is open to current undergraduate students, or students who graduated within the last four months, in all branches of chemistry. Posters may be based on research done as part of an undergraduate course, co-op project, or summer job in a university, government or industrial setting. Graduate students, who have not completed more than two semesters of their graduate studies program, may present a poster on work done as an undergraduate student on the condition that the poster topic is different from their current research topic.
Abstract Submission Dates Abstracts must be submitted on-line beginning March 10, 2007; the deadline for receipt of abstracts for the Undergraduate Student Poster Competition is midnight (EST), Wednesday, April 18, 2007. Please visit the conference Web site (www.csc2007.ca) for more information about poster specifications, travel assistance, conference registration, and accommodation.
DEADLINE:
April 18,
2007
90e CONGRÈS ET EXPOSITION CANADIENS DE CHIMIE
Présentation d’affiches des étudiants de 1er cycle Travaillez-vous présentement à un projet de recherche et souhaitez-vous partager vos résultats? Présentez-vous un exposé à un Congrès pour étudiants de 1er cycle en chimie de la Société canadienne de chimie (SCC) et aimeriez-vous le présenter à nouveau sous forme d’affiche? Aimeriez-vous présenter une affiche pour la première fois? Voici l’occasion de démontrer à vos pairs et aux professionnels en chimie ce dont vous êtes capable. Le 90e Congrès et exposition canadiens de chimie de la SCC aura lieu du 26 au 30 mai 2007 à Winnipeg (Manitoba). Nous vous invitons à participer à la présentation d’affiches des étudiants de 1er cycle que se tiendra durant l’événement. Les affiches peuvent être présentées dans les domaines de la chimie analytique, inorganique, organique et physique ainsi que de la biochimie. Deux prix seront remis dans chaque domaine (1er prix de 150 $ et 2e prix de 50 $). Ces montants peuvent augmenter selon le nombre de participants. Une aide de voyage est disponible pour les étudiants de 1er cycle qui assistent au congrès.
Admissibilité
Ce concours est ouvert aux étudiants actuellement au 1er cycle, ou aux étudiants qui ont obtenu leur diplôme moins de quatre mois auparavant, dans tous les secteurs de la chimie. Les affiches peuvent traiter de la recherche effectuée dans le cadre d’un cours de 1er cycle, d’un projet coopératif ou d’un emploi d’été dans un environnement universitaire, gouvernemental ou industriel. Les étudiants des cycles supérieurs qui n’ont pas complété plus de deux trimestres de leur programme peuvent soumettre une affiche portant sur le travail effectué en tant qu’étudiant de 1er cycle, à condition que le sujet de l’affiche diffère de celui du sujet de recherche actuel.
Dates de soumission des résumés Les résumés doivent être transmis en ligne à compter du 10 mars 2007. La date limite de réception des résumés pour la présentation des affiches des étudiants de 1er cycle est le mercredi 18 avril 2007 à minuit (HNE). Veuillez consulter le site Web du congrès (www.csc2007.ca) pour de plus amples renseignements sur les caractéristiques des affiches, l’aide de voyage, l’inscription au congrès et l’hébergement.
DATE LIMITE : le
18 avril
2007
Nominations are now open for
The Chemical Institute of Canada
2008AWARDSAct now!
Do you know an outstanding person who deserves to be recognized?
The Chemical Institute of Canada Medal is presented as a mark of distinction and recognition to a person who has made an outstanding contribution to the science of chemistry or chemical engineering in Canada. Sponsored by the Chemical Institute of Canada. Award: A medal and travel expenses.
The MontrĂŠal Medal is presented as a mark of distinction and honour to a resident in Canada who has shown significant leadership in or has made an outstanding contribution to the profession of chemistry or chemical engineering in Canada. In determining the eligibility for nominations for the award, administrative contributions within The Chemical Institute of Canada and other professional organizations that contribute to the advancement of the professions of chemistry and chemical engineering shall be given due consideration. Contributions to the sciences of chemistry and chemical engineering are not to be considered. Sponsored by the MontrĂŠal CIC Local Section. Award: A medal and travel expenses.
The Environmental Improvement Award is presented to a Canadian company, individual, team, or organization for a significant achievement in pollution prevention, treatment, or remediation. Sponsored by the CIC Environment Division. Award: A plaque and travel assistance.
The Macromolecular Science and Engineering Award is presented to an individual who, while residing in Canada, has made a distinguished contribution to macromolecular science or engineering. Sponsored by NOVA Chemicals Ltd. Award: A framed scroll, a cash prize, and travel expenses.
The CIC Award for Chemical Education (formerly the Union Carbide Award) is presented as a mark of recognition to a person who has made an outstanding contribution in Canada to education at the post-secondary level in the field of chemistry or chemical engineering. Sponsored by the CIC Chemical Education Fund. Award: A framed scroll and a cash prize.
Deadlines The deadline for all CIC awards is July 3, 2007 for the 2008 selection.
Nomination Procedure Submit your nominations to: Awards Manager The Chemical Institute of Canada 130 Slater Street, Suite 550 Ottawa, ON K1P 6E2 Tel.: 613-232-6252, ext. 223 Fax: 613-232-5862 awards@cheminst.ca Nomination forms and the full Terms of Reference for these awards are available at www.cheminst.ca/awards
Nominations are now open for
The Canadian Society for Chemistry
2008AWARDSAct now!
Do you know an outstanding person who deserves to be recognized?
The Alcan Award is presented to a scientist residing in Canada who has made a distinguished contribution in the fields of inorganic chemistry or electrochemistry while working in Canada. Sponsored by Alcan International Ltd. Award: A framed scroll, a cash prize, and travel expenses.
The Alfred Bader Award is presented as a mark of distinction and recognition for excellence in research in organic chemistry carried out in Canada. Sponsored by Alfred Bader, HFCIC. Award: A framed scroll, a cash prize, and travel expenses.
The Strem Chemicals Award for Pure or Applied Inorganic Chemistry is presented to a Canadian citizen or landed immigrant who has made an outstanding contribution to inorganic chemistry while working in Canada, and who is within ten years of his or her first professional appointment as an independent researcher in an academic, government, or industrial sector. Sponsored by Strem Chemicals Ltd. Award: A framed scroll and travel expenses for a lecture tour.
The Boehringer Ingelheim Award
of University Chemistry Chairs (CCUCC).
Award: A framed scroll, a cash prize, and travel expenses.
The Maxxam Award is presented to a scientist residing in Canada who has made a distinguished contribution in the field of analytical chemistry while working in Canada. Sponsored by Maxxam Analytics Inc. Award: A framed scroll, a cash prize, and travel expenses. The R. U. Lemieux Award is presented to an organic chemist who has made a distinguished contribution to any area of organic chemistry while working in Canada. Sponsored by the CIC Organic Chemistry Division. Award: A framed scroll, a cash prize, and travel expenses. The Merck Frosst Centre for Therapeutic Reasearch Award is presented to a scientist residing in Canada, who shall not have reached the age of 40 years by April 1 of the year of nomination and who has made a distinguished contribution in the fields of organic chemistry or biochemistry while working in Canada. Sponsored by Merck Frosst Canada Ltd. Award: A framed scroll, a cash prize, and travel expenses.
is presented to a Canadian citizen or landed immigrant whose PhD thesis in the field of organic or bioorganic chemistry was formally accepted by a Canadian university in the 12-month period preceding the nomination deadline of July 3 and whose doctoral research is judged to be of outstanding quality. Sponsored by Boehringer Ingelheim (Canada) Ltd. Award: A framed scroll, a cash prize, and travel expenses.
to a scientist residing in Canada who has made a distinguished contribution to the field of medicinal chemistry through research involving biochemical or organic chemical mechanisms. Sponsored by Bristol Myers Squibb Canada Co. Award: A framed scroll and a cash prize.
The Clara Benson Award is presented in recognition of a distinguished contribution to chemistry by a woman while working in Canada. Sponsored by the Canadian Council
an individual who demonstrates innovation in research in the field of analytical chemistry, where the research is anticipated to have significant potential for practical applications. The award is open to new faculty members at
The Bernard Belleau Award is presented
The Fred Beamish Award is presented to
a Canadian university and they must be recent graduates with six years of appointment. Sponsored by Eli Lilly Canada Inc. Award: A framed scroll, a cash prize, and travel expenses.
The Keith Laidler Award is presented to a scientist who has made a distinguished contribution in the field of physical chemistry while working in Canada . The award recognizes early achievement in the awardeeâ&#x20AC;&#x2122;s independent research career. Sponsored by Systems for Research. Award: A framed scroll and a cash prize. The W. A. E. McBryde Medal is presented to a young scientist working in Canada who has made a significant achievement in pure or applied analytical chemistry. Sponsored by Sciex Inc., Division of MDS Health Group. Award: A medal and a cash prize.
Deadline The deadline for all CSC awards is July 3, 2007 for the 2008 selection.
Nomination Procedure Submit your nominations to: Awards Manager The Canadian Society for Chemistry 130 Slater Street, Suite 550 Ottawa, ON K1P 6E2 Tel.: 613-232-6252, ext. 223 Fax: 613-232-5862 awards@cheminst.ca Nomination forms and the full Terms of Reference for these awards are available at www.chemistry.ca/awards
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