B | Acidity Constants for Some Organic Compounds

B • Acidity Constants for Some Organic Compounds

B • 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
${\text{HO}}_2\text{CC}\text{≡}{\text{CCO}}_2\text{H}$	1.2; 2.5
HO2CCO2H	1.2; 3.7
CHCl2CO2H	1.3
CH2(NO2)CO2H	1.3
$\text{HC}\text{≡}{\text{CCO}}_2\text{H}$	1.9
(Z) ${\text{HO}}_2\text{CCH}═{\text{CHCO}}_2\text{H}$	1.9; 6.3
	2.4
CH3COCO2H	2.4
NCCH2CO2H	2.5
${\text{CH}}_3\text{C}\text{≡}{\text{CCO}}_2\text{H}$	2.6
CH2FCO2H	2.7
CH2ClCO2H	2.8
HO2CCH2CO2H	2.8; 5.6
CH2BrCO2H	2.9
	3.0
	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
${\text{H}}_2\text{C}\text{═}{\text{CHCO}}_2\text{H}$	4.2
HO2CCH2CH2CO2H	4.2; 5.7
HO2CCH2CH2CH2CO2H	4.3; 5.4
	4.5
${\text{H}}_2\text{C}\text{═}{\text{C(CH}}_3{\text{)CO}}_2\text{H}$	4.7
CH3CO2H	4.8
CH3CH2CO2H	4.8
(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
	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
${{\text{(CH}}_3\text{)}}_2\text{C}\text{═}\text{NOH}$	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
${\text{H}}_2\text{C}\text{═}{\text{CHCH}}_2\text{OH}$	15.5
CH3CH2OH	16.0
CH3CH2CH2OH	16.1
CH3COCH2Br	16.1
	16.7
CH3CHO	17
(CH3)2CHCHO	17
(CH3)2CHOH	17.1
(CH3)3COH	18.0
CH3COCH3	19.3
	23
CH3CO2CH2CH3	25
$\text{HC}\text{≡}\text{CH}$	25
CH3CN	25
CH3SO2CH3	28
(C6H5)3CH	32
(C6H5)2CH2	34
CH3SOCH3	35
NH3	36
CH3CH2NH2	36
(CH3CH2)2NH	40
	41
	43
${\text{H}}_2\text{C}\text{═}{\text{CH}}_2$	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.