ALCOHOLS and other OXYGEN ACIDS Alcohols Compound pK Ref. Choline 13.9 6 Chloral hydrate 9.66, 11.0 61 Trifluoroethanol 12.5 CF3 CH2 OH 11.4, 12.43 63 CF3 CH(OH)CH3 11.8 63 CF3 CH2 (CH3 )3OH 12.43 10 C3 F7 CH2 OH 11.4** 63 (C3 F7 )2 CHOH 10.6** 63 HCCCH2 OH 13.55 64 C(CH2 OH))4 14.1 64 HOCH2 CHOHCH2 OH 4.4 64 HOCH2 CH2 OH 14.77 64 CH3 CCH2 OH 14.82 64 CH3 OH 15.54 CH2 =CHCH2 OH 15.52 H2 O 15.74 64 CH3 CH2 OH 16 64 Substituent effects for ionization of RCH2OH R CCl-3 12.24,11.80 64,65 CF312.37 64 CHF2 CH2 12.74 64 CHCl2 12.89 64 CHEC13.55 64 H2 Cl14.31 64 CH3 CCH2 14.8 64 HOCH2 15.1 H15.5 64 CH2 =CH15.5 64 CH3 -(extrap) (15.9) 64 CF3 C(CH3 )2 OH 11.6 64 HOCH2 CF2 CH2 OH 11 64 Primary alcohols=R•CH2 •OH and Secondary alcohols in 50% alcohol C2 F5 11.35 65 C4 F9 11.35 65 C5 F11 11.37 65 C7 F15 11.35 65 CHF2 12.00 65 CF2 Cl 11.63 65 CHF2 CF2 11.34 65 CHF2 • (CF2 )2 11.35 65 CF3 • CH2 12.7 65 CF3 • (CH2 )2 12.9 65 CF3 • CHMe • OH 11.28 65 C3 F7 • CHMe • OH 11.38 65 C3 F7 CHEt • OH 11.37 65 C3 F7 CHPr • OH 11.37 65 C3 F7 • CH(CF3 ) • OH 10.46 65
Compound pK C3 F7 •CH(C2 F5) •OH 10.48 (C3 F7 )2 CH•OH 10.52 62 Carbonium ions Triphenylmethanols in H 2SO 4 4,4,4-Trimethoxy 4,4’-Dimethoxy -1.24 4-Methoxy -3.40 4-Methyl -5.41 4 -Trideuteriomethyl5.43 3,3’,3”-Trimethyl6.35 Unsubstituted triphenylmethanol6.63 64 4,4;,4;-Trichloro64 4 -NitroCCl3 CH2 OH 11.8*** CF3 CH2 OH 11.3*** Hydroxamic acids FuroGlycine HippuroisoNicotin 64 p-MethylbenzNicotinNicotin-methiodide m-NitrobenzPicolin Pyrimidine-2-carboxSalicylTropoOther oxygen acids Trimethylamine-n-oxide Dimethylglyoxime (50% dioxane) O-methyl ether Tropolone α -Bromotropolone Acetald hydrate Formald hydrate a 50% dioxane ***50 aquaeous ethanol
8.45 7.40 8.80 7.85 6.46 8.07 8.50 7.88 7.43
4.6 12.92 12a 6.95a 13.48 13.29
Ref. 65 65 HC1O4 HNO3 .82. .82 -1.14 -1.11 -3.59 -3.41 -5.67 5.67 -5.95 -6.89
8.90 8.30
9.09
12.84
6.60 7.749.15-
ref .80 66 66 66 66 66 66 8.01 9.76
72 72 72 72 72 72 72 72 72
18 77 77 77 91 91
66
66 66
72 72
72
77