Appendix B | Acidity Constants for Some Organic Compounds
Acidity Constants for Some Organic Compounds Table B1
|
Compound |
pKa |
|
CH3SO3H |
−1.8 |
|
CH(NO2)3 |
0.1 |
|
|
0.3 |
|
CCl3CO2H |
0.5 |
|
CF3CO2H |
0.5 |
|
CBr3CO2H |
0.7 |
|
HO!CC≡CCO!H |
1.2; 2.5 |
|
HO2CCO2H |
1.2; 3.7 |
|
CHCl2CO2H |
1.3 |
|
CH2(NO2)CO2H |
1.3 |
|
HC≡CCO!H |
1.9 |
|
(Z) HO!CCH═CHCO!H |
1.9; 6.3 |
|
|
2.4 |
|
CH3COCO2H |
2.4 |
|
NCCH2CO2H |
2.5 |
|
CH“C≡CCO!H |
2.6 |
|
CH2FCO2H |
2.7 |
|
CH2ClCO2H |
2.8 |
|
HO2CCH2CO2H |
2.8; 5.6 |
|
CH2BrCO2H |
2.9 |
|
|
3.0 |
|
Compound |
pKa |
|
|
3.0 |
|
CH2ICO2H |
3.2 |
|
CHOCO2H |
3.2 |
|
|
3.4 |
|
|
3.5 |
|
HSCH2CO2H |
3.5; 10.2 |
|
CH2(NO2)2 |
3.6 |
|
CH3OCH2CO2H |
3.6 |
|
CH3COCH2CO2H |
3.6 |
|
HOCH2CO2H |
3.7 |
|
HCO2H |
3.7 |
|
|
3.8 |
|
|
4.0 |
|
CH2BrCH2CO2H |
4.0 |
|
|
4.1 |
|
|
4.2 |
|
H!C═CHCO!H |
4.2 |
|
HO2CCH2CH2CO2H |
4.2; 5.7 |
|
HO2CCH2CH2CH2CO2H |
4.3; 5.4 |
|
|
4.5 |
|
H!C═C(CH”)CO!H |
4.7 |
|
CH3CO2H |
4.8 |
|
CH3CH2CO2H |
4.8 |
|
Compound |
pKa |
|
(CH3)3CCO2H |
5.0 |
|
CH3COCH2NO2 |
5.1 |
|
|
5.3 |
|
O2NCH2CO2CH3 |
5.8 |
|
|
5.8 |
|
|
6.2 |
|
|
6.6 |
|
HCO3H |
7.1 |
|
|
7.2 |
|
(CH3)2CHNO2 |
7.7 |
|
|
7.8 |
|
CH3CO3H |
8.2 |
|
|
8.5 |
|
CH3CH2NO2 |
8.5 |
|
|
8.7 |
|
CH3COCH2COCH3 |
9.0 |
|
|
9.3; 11.1 |
|
|
9.3; 12.6 |
|
Compound |
pKa |
|
|
9.4 |
|
|
9.9; 11.5 |
|
|
9.9 |
|
CH3COCH2SOCH3 |
10.0 |
|
|
10.3 |
|
CH3NO2 |
10.3 |
|
CH3SH |
10.3 |
|
CH3COCH2CO2CH3 |
10.6 |
|
CH3COCHO |
11.0 |
|
CH2(CN)2 |
11.2 |
|
CCl3CH2OH |
12.2 |
|
Glucose |
12.3 |
|
(CH”)!C═NOH |
12.4 |
|
CH2(CO2CH3)2 |
12.9 |
|
CHCl2CH2OH |
12.9 |
|
CH2(OH)2 |
13.3 |
|
HOCH2CH(OH)CH2OH |
14.1 |
|
CH2ClCH2OH |
14.3 |
|
|
15.0 |
|
|
15.4 |
|
CH3OH |
15.5 |
|
H!C═CHCH!OH |
15.5 |
|
CH3CH2OH |
16.0 |
|
CH3CH2CH2OH |
16.1 |
|
CH3COCH2Br |
16.1 |
|
|
16.7 |
|
CH3CHO |
17 |
|
Compound |
pKa |
|
(CH3)2CHCHO |
17 |
|
(CH3)2CHOH |
17.1 |
|
(CH3)3COH |
18.0 |
|
CH3COCH3 |
19.3 |
|
|
23 |
|
CH3CO2CH2CH3 |
25 |
|
HC≡CH |
25 |
|
CH3CN |
25 |
|
CH3SO2CH3 |
28 |
|
(C6H5)3CH |
32 |
|
(C6H5)2CH2 |
34 |
|
CH3SOCH3 |
35 |
|
NH3 |
36 |
|
CH3CH2NH2 |
36 |
|
(CH3CH2)2NH |
40 |
|
|
41 |
|
|
43 |
|
H!C═CH! |
44 |
|
CH4 |
∼60 |
An acidity list covering more than 5000 organic compounds has been published: E.P. Serjeant and B. Dempsey (eds.), “Ionization Constants of Organic Acids in Aqueous Solution,” IUPAC Chemical Data Series No. 23, Pergamon Press, Oxford, 1979.
