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32: Appendix
32.1: Appendix B - Acidity Constants for Some Organic Compounds

32.1: Appendix B - Acidity Constants for Some Organic Compounds

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Table B1: Acidity Constants for Some Organic Compounds
Compound	pK_a
CH₃SO₃H	−1.8
CH(NO₂)₃	0.1
	0.3
CCl₃CO₂H	0.5
CF₃CO₂H	0.5
CBr₃CO₂H	0.7
${HO}_{2} CC ≡ {CCO}_{2} H$	1.2; 2.5
HO₂CCO₂H	1.2; 3.7
CHCl₂CO₂H	1.3
CH₂(NO₂)CO₂H	1.3
$HC ≡$ ${CCO}_{2} H$	1.9
(Z) ${HO}_{2} CCH ═ {CHCO}_{2} H$	1.9; 6.3
	2.4
CH₃COCO₂H	2.4
NCCH₂CO₂H	2.5
${CH}_{3} C ≡ {CCO}_{2} H$	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
$H_{2} C ═ {CHCO}_{2} H$	4.2
HO₂CCH₂CH₂CO₂H	4.2; 5.7
HO₂CCH₂CH₂CH₂CO₂H	4.3; 5.4
	4.5
$H_{2} C ═ C({CH}_{3}) {CO}_{2} H$	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
$($ ${CH}_{3})_{2} C ═ NOH$	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
$H_{2} C ═ {CHCH}_{2} OH$	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
$HC ≡$ $CH$	25
CH₃CN	25
CH₃SO₂CH₃	28
(C₆H₅)₃CH	32
(C₆H₅)₂CH₂	34
CH₃SOCH₃	35
NH₃	36
CH₃CH₂NH₂	36
(CH₃CH₂)₂NH	40
	41
	43
$H_{2} C ═ {CH}_{2}$	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.

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