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APPE N DIX G Acid Dissociation Constants

Ionic strength (␮) ⴝ 0 ␮  0.1 M§

Name Structure* pKa† Ka‡ pKa†
Acetic acid CH3CO2H 4.756 1.75  105 4.56
(ethanoic acid)

NH3

Alanine CHCH3 2.344 (CO2H) 4.53  103 2.33

9.868 (NH3) 1.36  1010 9.71
CO2H

Aminobenzene NH3 4.601 2.51  105 4.64

(aniline)

4-Aminobenzenesulfonic acid O S
3
NH3 3.232 5.86  104 3.01
(sulfanilic acid)

NH3
2-Aminobenzoic acid 2.08 (CO2H) 8.3  103 2.01
(anthranilic acid) 4.96 (NH3) 1.10  105 4.78
CO2H

2-Aminoethanethiol HSCH2CH2NH3 —— 8.21 (SH)

(2-mercaptoethylamine) —— 10.73 (NH3)

2-Aminoethanol HOCH2CH2NH3 9.498 3.18  1010 9.52

(ethanolamine)

OH
4.70 (NH3) (20°) 2.0  105 4.74
2-Aminophenol
9.97 (OH) (20°) 1.05  1010 9.87
NH3

Ammonia NH4 9.245 5.69  1010 9.26

NH3
NH2 1.823 (CO2H) 1.50  102 2.03
Arginine CHCH2CH2CH2NHC 8.991 (NH3) 1.02  109 9.00
NH2 —— (NH2) —— (12.1)
CO2H

O
2.24 5.8  103 2.15
Arsenic acid HO As OH 6.96 1.10  107 6.65
(hydrogen arsenate) (11.50) 3.2  1012 (11.18)
OH

Arsenious acid As(OH)3 9.29 5.1  1010 9.14

(hydrogen arsenite)

NH3 O

Asparagine CHCH2CNH2 —— —— 2.16 (CO2H)

—— —— 8.73 (NH3)
CO2H

*Each acid is written in its protonated form. The acidic protons are indicated in bold type.
†
pKa values refer to 25⬚C unless otherwise indicated. Values in parentheses are considered to be less reliable. Data are from
A. E. Martell, R. M. Smith, and R. J. Motekaitis, NIST Database 46 (Gaithersburg, MD: National Institute of Standards and
Technology, 2001).
‡
The accurate way to calculate Kb for the conjugate base is pKb  13.995  pKa and Kb  10pKb.
§
See marginal note on page 166 for distinction between pKa at ␮  0 and at ␮  0.1 M.
(Continued)

APPENDIX G Acid Dissociation Constants AP11

harxxxxx_App-G.qxd 2/15/10 5:25 PM Page AP12

Ionic strength (␮) ⴝ 0 ␮  0.1 M

Name Structure pKa Ka pKa
NH3
1.990 (-CO2H) 1.02  102 1.95
Aspartic acid CHCH2CO2H 3.900 ( -CO2H) 1.26  104 3.71
10.002 (NH3) 9.95  1011 9.96
 CO2H

——
Aziridine NH2 8.04 9.1  109
(dimethyleneimine)

CO2H 2.86 1.38  103 2.67

Benzene-1,2,3-tricarboxylic acid CO2H 4.30 5.0  105 3.91
(hemimellitic acid) 6.28 5.2  107 5.50

CO2H

Benzoic acid CO2H 4.202 6.28  105 4.01

Benzylamine CH2NH3 9.35 4.5  1010 9.40

—— —— (1.3)
2,2-Bipyridine 4.34 4.6  105 4.41
N N
H H
9.237 5.79  1010 8.98
Boric acid B(OH)3 (12.74) (20°) 1.82  1013 ——
(hydrogen borate) (13.80) (20°) 1.58  1014 ——

Bromoacetic acid BrCH2CO2H 2.902 1.25  103 2.71

HON NOH
Butane-2,3-dione dioxime 10.66 2.2  1011 10.45
(dimethylglyoxime) CH3 CH3 (12.0) 1  1012 (11.9)

Butanoic acid CH3CH2CH2CO2H 4.818 1.52  105 4.62

CO2H
cis-Butenedioic acid 1.92 1.20  102 1.75
(maleic acid) CO2H 6.27 5.37  107 5.84

CO2H
trans-Butenedioic acid 3.02 9.5  104 2.84
(fumaric acid) HO2C 4.48 3.3  105 4.09

Butylamine CH3CH2CH2CH2NH3 10.640 2.29  1011 10.66

O
Carbonic acid* 6.351 4.46  107 6.13
(hydrogen carbonate) HO C OH 10.329 4.69  1011 9.91

Chloroacetic acid ClCH2CO2H 2.865 1.36  103 2.69

3-Chloropropanoic acid ClCH2CH2CO2H 4.11 7.8  105 3.92

Chlorous acid HOCl£O 1.96 1.10  102 ——

(hydrogen chlorite)

*The concentration of “carbonic acid” is considered to be the sum [H2CO3]  [CO2(aq)]. See Box 6-4.

AP12 APPENDIX G Acid Dissociation Constants

harxxxxx_App-G.qxd 2/15/10 5:25 PM Page AP13

Ionic strength (␮) ⴝ 0 ␮  0.1 M

Name Structure pKa Ka pKa
O

Chromic acid HO Cr OH (0.2) (20°) 1.6 (0.6) (20

C)
(hydrogen chromate) 6.51 3.1  107 6.05
O

Citric acid CO2H 3.128 7.44  104 2.90

(2-hydroxypropane-1,2,3- 4.761 1.73  105 4.35
tricarboxylic acid) HO2CCH2CCH2CO2H 6.396 4.02  107 5.70
OH

Cyanoacetic acid NCCH2CO2H 2.472 3.37  103 ——

Cyclohexylamine NH3 10.567 2.71  1011 10.62

NH3 (1.7) (CO2H) 2  102 (1.90)

Cysteine 8.36 (SH) 4.4  109 8.18
CHCH2SH 10.74 (NH3) 1.82  1011 10.30
CO2H

Dichloroacetic acid Cl2CHCO2H (1.1) 8  102 (0.9)

Diethylamine (CH3CH2)2NH2 11.00 1.0  1011 11.04

OH
1,2-Dihydroxybenzene 9.45 3.5  1010 9.26
(catechol) —— —— (13.3)
OH

OH
1,3-Dihydroxybenzene —— —— 9.30
(resorcinol) —— —— 11.06
OH

OH

D-2,3-Dihydroxybutanedioic HO2CCHCHCO2H 3.036 9.20  104 2.82

acid (D-tartaric acid) 4.366 4.31  105 3.97
OH

HOCH2CHCH2SH
2,3-Dimercaptopropanol —— —— 8.63
SH —— —— 10.65

Dimethylamine (CH3)2NH2 10.774 1.68  1011 10.81

NO2
2,4-Dinitrophenol 4.114 7.69  105 3.92
O2N OH

Ethane-1,2-dithiol HSCH2CH2SH —— —— 8.85 (30

C)
—— —— 10.43 (30
C)

Ethylamine CH3CH2NH3 10.673 2.12  1011 10.69

Ethylenediamine 
H3NCH2CH2NH3
 6.848 1.42  107 7.11
(1,2-diaminoethane) 9.928 1.18  1010 9.92

(Continued)

APPENDIX G Acid Dissociation Constants AP13

harxxxxx_App-G.qxd 2/15/10 5:25 PM Page AP14

Ionic strength (␮) ⴝ 0 ␮  0.1 M

Name Structure pKa Ka pKa
—— (CO2H) —— (0.0) (CO2H) (  1 M)
—— (CO2H) —— (1.5) (CO2H)
 
Ethylenedinitrilotetraacetic (HO2CCH2)2NHCH2CH2NH(CH2CO2H)2 —— (CO2H) —— 2.00 (CO2H)
acid (EDTA) —— (CO2H) —— 2.69 (CO2H)
6.273 (NH) 5.3  107 6.13 (NH)
10.948 (NH) 1.13  1011 10.37 (NH)

Formic acid HCO2H 3.744 1.80  104 3.57

(methanoic acid)
NH3
 2.160 (-CO2H) 6.92  103 2.16
Glutamic acid CHCH2CH2CO2H 4.30 (-CO2H) 5.0  105 4.15
9.96 (NH3) 1.10  1010 9.58
 CO2H

NH3 O

Glutamine CHCH2CH2CNH2 —— —— 2.19 (CO2H)

—— —— 9.00 (NH3)
CO2H

NH3

Glycine CH2 2.350 (CO2H) 4.47  103 2.33

(aminoacetic acid) 9.778 (NH3) 1.67  1010 9.57
CO2H

NH
2
Guanidine —— —— (13.5) (  1 M)
H2N C NH2

1,6-Hexanedioic acid
HO2CCH2CH2CH2CH2CO2H
4.424 3.77  105 4.26
(adipic acid) 5.420 3.80  106 5.04

O O
Hexane-2,4-dione 9.38 4.2  1010 9.11 (20
C)
CH3CCH2CCH2CH3

NH3
NH (1.6) (CO2H) 3  102 (1.7)
Histidine CHCH2  5.97 (NH) 1.07  106 6.05
N 9.28 (NH3) 5.2  1010 9.10
CO2H H

 
Hydrazine H3N  NH3 0.99 1.0  101 (0.21) (  0.5 M)
7.98 1.05  108 8.07

 
Hydrazoic acid HN N N 4.65 2.2  105 4.45
(hydrogen azide)

Hydrogen cyanate HOCΩN 3.48 3.3  104 ——

10
Hydrogen cyanide HCΩN 9.21 6.2  10 9.04

Hydrogen fluoride HF 3.17 6.8  104 2.94

Hydrogen peroxide HOOH 11.65 2.2  1012 ——

8
Hydrogen sulfide H2S 7.02 9.5  10 6.82
14.0* 1.0  1014* ——

Hydrogen thiocyanate HSCΩN (1.1) (20°C) 1.3  101 ——

4
Hydroxyacetic acid HOCH2CO2H 3.832 1.48  10 3.62
(glycolic acid)
*D. J. Phillips and S. L. Phillips. “High Temperature Dissociation Constants of HS and the Standard Thermodynamic Values for S2,”
J. Chem. Eng. Data 2000, 45, 981.

AP14 APPENDIX G Acid Dissociation Constants

harxxxxx_App-G.qxd 2/15/10 5:25 PM Page AP15

Ionic strength (␮) ⴝ 0 ␮  0.1 M

Name Structure pKa Ka pKa
Hydroxybenzene OH 9.997 1.01  1010 9.78
(phenol)

CO2H
2-Hydroxybenzoic acid 2.972 (CO2H) 1.07  103 2.80
(salicylic acid) OH (13.7) (OH) 2  1014 (13.4)

L-Hydroxybutanedioic acid OH 3.459 3.48  104 3.24

(malic acid) HO2CCH2CHCO2H 5.097 8.00  106 4.68


Hydroxylamine HONH3 5.96 (NH) 1.10  106 5.96
(13.74) (OH) 1.8  1014 ——

8-Hydroxyquinoline 4.94 (NH) 1.15  105 4.97

(oxine) N 9.82 (OH) 1.51  1010 9.65
H
HO

Hypobromous acid HOBr 8.63 2.3  109 ——

(hydrogen hypobromite)

Hypochlorous acid HOCl 7.53 3.0  108 ——

(hydrogen hypochlorite)

Hypoiodous acid HOI 10.64 2.3  1011 ——

(hydrogen hypoiodite)

O
Hypophosphorous acid (1.3) 5  102 (1.1)
(hydrogen hypophosphite) H2POH

Imidazole NH 6.993 1.02  107 7.00

(1,3-diazole) (14.5) 3  1015 ——
N
H


(1.85) (CO2H) 1.41  102 (1.77)
Iminodiacetic acid H2N(CH2CO2H)2 2.84 (CO2H) 1.45  103 2.62
9.79 (NH2 ) 1.62  1010 9.34

O
Iodic acid 0.77 0.17 ——
(hydrogen iodate) HOI O

Iodoacetic acid ICH2CO2H 3.175 6.68  104 2.98

NH3

Isoleucine CHCH(CH3)CH2CH3 2.318 (CO2H) 4.81  103 2.26

9.758 (NH3) 1.75  1010 9.60
CO2H

NH3

Leucine CHCH2CH(CH3)2 2.328 (CO2H) 4.70  103 2.32

9.744 (NH3) 1.80  1010 9.58
CO2H

 NH
3
 (1.77) (CO2H) 1.7  102 2.15
Lysine CHCH2CH2CH2CH2NH3 9.07 (-NH3) 8.5  1010 9.15
10.82 (-NH3) 1.51  1011 10.66
CO2H

(Continued)

APPENDIX G Acid Dissociation Constants AP15

harxxxxx_App-G.qxd 2/15/10 5:25 PM Page AP16

Ionic strength (␮) ⴝ 0 ␮  0.1 M

Name Structure pKa Ka pKa
Malonic acid HO2CCH2CO2H 2.847 1.42  103 2.65
(propanedioic acid) 5.696 2.01  106 5.27

Mercaptoacetic acid HSCH2CO2H 3.64 (CO2H) 2.3  104 3.48

(thioglycolic acid) 10.61 (SH) 2.5  1011 10.11

2-Mercaptoethanol HSCH2CH2OH 9.72 1.9  1010 9.40

NH3
Methionine CHCH2CH2SCH3 —— —— 2.18 (CO2H)
—— —— 9.08 (NH3)
CO2H

OCH3
2-Methoxyaniline 4.526 2.98  105 ——

(o-anisidine) NH3

4-Methoxyaniline CH3O

NH3 5.357 4.40  106 5.33
( p-anisidine)

 10.65
Methylamine CH3NH3 10.632 2.33  1011

CH3
2-Methylaniline 4.447 3.57  105 ——
(o-toluidine) 
NH3

4-Methylaniline  5.080 8.32  106 5.09

( p-toluidine) CH3 NH3

CH3
2-Methylphenol 10.31 4.9  1011 10.09
(o-cresol) OH

4-Methylphenol 10.269 5.5  1011 10.04

CH3 OH
( p-cresol)

Morpholine 8.492 3.22  109 ——

(perhydro-1,4-oxazine)
O NH2

CO2H
1-Naphthoic acid 3.67 2.1  104 ——

CO2H ——
2-Naphthoic acid 4.16 6.9  105

OH
1-Naphthol 9.416 3.84  1010 9.14

OH
2-Naphthol 9.573 2.67  1010 9.31

—— (CO2H) —— (1.0)
 2.0 (CO2H) (25°) 0.010 1.81
Nitrilotriacetic acid HN(CH2CO2H)3 2.940 (CO2H) (20°) 1.15  103 2.52
10.334 (NH) (20°) 4.63  1011 9.46

AP16 APPENDIX G Acid Dissociation Constants

harxxxxx_App-G.qxd 2/15/10 10:24 PM Page AP17

Ionic strength (␮) ⴝ 0 ␮ ⫽ 0.1 M

Name Structure pKa Ka pKa
NO2
2-Nitrobenzoic acid 2.185 6.53 ⫻ 10⫺3 ——
CO2H

NO2

3-Nitrobenzoic acid 3.449 3.56 ⫻ 10⫺4 3.28

CO2H

4-Nitrobenzoic acid O2N CO2H 3.442 3.61 ⫻ 10⫺4 3.28

Nitroethane CH3CH2NO2 8.57 2.7 ⫻ 10⫺9 ——

NO2
2-Nitrophenol 7.230 5.89 ⫻ 10⫺8 7.04
OH

NO2

3-Nitrophenol 8.37 4.3 ⫻ 10⫺9 8.16

OH

4-Nitrophenol O2N OH 7.149 7.10 ⫻ 10⫺8 6.96

NO
N-Nitrosophenylhydroxylamine N —— —— 4.16
(cupferron) OH

Nitrous acid HON£O 3.15 7.1 ⫻ 10⫺4 ——

Oxalic acid HO2CCO2H 1.250 5.62 ⫻ 10⫺2 (1.2)

(ethanedioic acid) 4.266 5.42 ⫻ 10⫺5 3.80

O
Oxoacetic acid 3.46 3.5 ⫻ 10⫺4 3.05
(glyoxylic acid) HCCO2H

O
Oxobutanedioic acid 2.56 2.8 ⫻ 10⫺3 2.26
(oxaloacetic acid) HO2CCH2CCO2H 4.37 4.3 ⫻ 10⫺5 3.90

O
2-Oxopentanedioic —— —— (1.9) (␮ ⫽ 0.5 M)
(␣-ketoglutaric acid) HO2CCH2CH2CCO2H —— —— 4.44 (␮ ⫽ 0.5 M)

O
2-Oxopropanoic acid 2.48 3.3 ⫻ 10⫺3 2.26
(pyruvic acid) CH3CCO2H

1,5-Pentanedioic acid HO2CCH2CH2CH2CO2H 4.345 4.52 ⫻ 10⫺5 4.19

(glutaric acid) 5.422 3.78 ⫻ 10⫺6 5.06
Pentanoic acid CH3CH2CH2CH2CO2H 4.843 1.44 ⫻ 10⫺5 4.63 (18⬚C)
(valeric acid)

1,10-Phenanthroline —— —— (1.8)
NH HN 4.91 1.23 ⫻ 10⫺5 4.92
⫹ ⫹

Phenylacetic acid CH2CO2H 4.310 4.90 ⫻ 10⫺5 4.11

(Continued)

APPENDIX G Acid Dissociation Constants AP17

harxxxxx_App-G.qxd 2/15/10 5:25 PM Page AP18

Ionic strength (␮) ⴝ 0 ␮  0.1 M

Name Structure pKa Ka pKa
NH3
Phenylalanine CHCH2 2.20 (CO2H) 6.3  103 2.18
9.31 (NH3) 4.9  1010 9.09
CO2H

O
2.148 7.11  103 1.92
Phosphoric acid* HO P OH 7.198 6.34  108 6.71
(hydrogen phosphate) 12.375 4.22  1013 11.52
OH

Phosphorous acid HP OH (1.5) 3  102 ——

(hydrogen phosphite) 6.78 1.66  107 ——
OH

CO2H
Phthalic acid 2.950 1.12  103 2.76
(benzene-1,2-dicarboxylic acid) CO2H 5.408 3.90  106 4.92

Piperazine   5.333 4.65  106 5.64

H2N NH2
(perhydro-1,4-diazine) 9.731 1.86  1010 9.74


Piperidine NH2 11.125 7.50  1012 11.08

Proline CO2H 1.952 (CO2H) 1.12  102 1.89

N

H2 10.640 (NH2 ) 2.29  1011 10.46

Propanoic acid CH3CH2CO2H 4.874 1.34  105 4.69

Propenoic acid H2C£CHCO2H 4.258 5.52  105 ——

(acrylic acid)

Propylamine CH3CH2CH2NH3 10.566 2.72  1011 10.64

Pyridine 5.20 6.3  106 5.24

NH
(azine)

NH
Pyridine-2-carboxylic acid (1.01) (CO2H) 9.8  102 (0.95)
(picolinic acid) CO2H 5.39 (NH) 4.1  106 5.21

HO2C
Pyridine-3-carboxylic acid 2.03 (CO2H) 9.3  103 2.08
(nicotinic acid) NH  4.82 (NH) 1.51  105 4.69

O
O CH —— —— (1.4) (POH)
Pyridoxal-5-phosphate HO POCH2 OH —— —— 3.51 (OH)
—— —— 6.04 (POH)
HO N
 CH3 —— —— 8.25 (NH)
H

Pyrophosphoric acid O O (0.9) 0.13 (0.8)

(hydrogen diphosphate) 2.28 5.2  103 (1.9)
(HO)2POP(OH)2 6.70 2.0  107 5.94
9.40 4.0  1010 8.25
*pK3 from A. G. Miller and J. W. Macklin, Anal. Chem. 1983, 55, 684.

AP18 APPENDIX G Acid Dissociation Constants

harxxxxx_App-G.qxd 2/15/10 5:25 PM Page AP19

Ionic strength (␮) ⴝ 0 ␮  0.1 M

Name Structure pKa Ka pKa
12
Pyrrolidine NH2 11.305 4.95  10 11.3

NH3

Serine CHCH2OH 2.187 (CO2H) 6.50  103 2.16

9.209 (NH3) 6.18  1010 9.05
CO2H

Succinic acid HO2CCH2CH2CO2H 4.207 6.21  105 3.99

(butanedioic acid) 5.636 2.31  106 5.24

Sulfuric acid HO S OH 1.987 (pK2 ) 1.03  102 1.54

(hydrogen sulfate)
O
O
Sulfurous acid 1.857 1.39  102 1.66
(hydrogen sulfite) HOSOH 7.172 6.73  108 6.85

O
Thiosulfuric acid HOSSH (0.6) 0.3 ——
(hydrogen thiosulfate) (1.6) 0.03 (1.3)
O

NH3

Threonine CHCHOHCH3 2.088 (CO2H) 8.17  103 2.20

9.100 (NH3) 7.94  1010 8.94
CO2H

Trichloroacetic acid Cl3CCO2H (0.5) 3 ——

 8
Triethanolamine (HOCH2CH2)3NH 7.762 1.73  10 7.85
 11
Triethylamine (CH3CH2)3NH 10.72 1.9  10 10.76

OH
1,2,3-Trihydroxybenzene OH —— —— 8.96
(pyrogallol) —— —— 11.00
—— —— (14.0) (20
C)
OH

Trimethylamine (CH3)3NH 9.799 1.59  1010 9.82

Tris(hydroxymethyl)amino- (HOCH2)3CNH3 8.072 8.47  109 8.10

methane (tris or tham)
NH3

Tryptophan CHCH2 —— —— 2.37 (CO2H)

N —— —— 9.33 (NH3)
CO2H
H

NH3
—— —— 2.41 (CO2H)
Tyrosine CHCH2 OH —— —— 8.67 (NH3)
—— —— 11.01 (OH)
CO2H

NH3

Valine CHCH(CH3)2 2.286 (CO2H) 5.18  103 2.27

9.719 (NH3) 1.91  1010 9.52
CO2H

Water* H2O 13.997 1.01  1014 ——

*The constant given for water is Kw.

APPENDIX G Acid Dissociation Constants AP19