[PDF] pKa Data Compiled by R. Williams pKa Values INDEX Inorganic 2

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pKa Data Compiled by R. Williams pKa Values INDEX

Inorganic2Phenazine24

Phosphates3Pyridine25

Carboxylic acids4, 8 Pyrazine26

Aliphatic4, 8

Aromatic7, 8Quinoline27

Phenols9Quinazoline27

Alcohols and oxygen acids10, 11Quinoxaline27

Amino Acids12 Special Nitrogen Compounds28

Peptides13 Hydroxylamines28

Nitrogen Compounds14 Hydrazines28

Aliphatic amines15, 17, 19 Semicarbazones28

Cyanoamines16 Amidoximes28

Anilines17, 18, 20 Thiols29

Nucleosides21 Carbon Acids30,31

Special Table Heterocycles22 Indicators31

Acridine23 References32-34

Benzoquinoline24

Cinnoline23

Hydantoin24

Imidazole24

For complex chelating agents, see also reference 77. Note. This document was compiled by W.P. Jencks and has been added to by

F.H. Westheimer

Provided by the ACS, Organic Division Updated 4/7/2022

Page 1

pKa Data Compiled by R. Williams ACIDS

Compound pKRef.H3PO22.0, 2.23*28

H

2PO4-7.21*77AgOH3.964HPO4_12.32*77Al(OH)311.228H3PO32.028As(OH)39.2228H2PO3-6.58*77H3AsO42.22, 7.0, 13.028H4P2O71.52*77H2AsO4-6.98*77H3 P2O7-2.36*77HAsO4*11.53*77H2P2O7=6.60*77As2O304

HP2O7=9.25*77H3AsO39.22*

H3BO39.23*28HReO4-1.2530

H2B4O74.0034HSCN4.0034

H2SeO32.6, 8.3, 2.62*28HB4O79.0034

HSeO38.3277Be(OH)23.74

H2SeO4Strong, 2.0 28HBr-9.0031

HOBr8.728HSeO42.0034

HOCl7.53, 7.4628, 33H3SiO310.034HClO22.028H2SO31.9, 7.0, 1.76*28, 77HClO3-1.0028H2SO4-3.0, 1.928HClO4 (70%)-10.0031HSO37.21*77CH3SO3H-0.631HSO4-1.99*77HCN9.4034H2S2O41.929H2CO36.37, 6.35*, 3.5834, 32H2Se3.89*77HCO310.33*HSe-11.00*77H2CrO4-0.9830H2S7.00*77HCrO46.50*2, 30HS-12.92*77HOCN3.9234HSbO211.034HZ3.17*, 0.59*77HTe5.0034H2GeO38.59, 12.7234, 78H2Te2.64, 11.034, 78Ge(OH)48.68, 12.728H2TeO32.7, 8.028HI-10.031Te(OH)66.2, 8.828HOI11.028H2VO4-8.9530HIO30.828

HVO

4=14.430H4IO6-6.0034

H2CrO40.7477H5IO61.64, 1.55, 8.2734, 28

HOCN3.7377HMnO4-2.2530HSCN0.8577NH3OH*5.98*H3PO21.0777NH4*9.24*77H3PO42.12*77HN34.72*77H2S2O30.60*, 1.72*77HNO23.2928H3AuO313.3, 16.078HNO328H3GaO310.32, 11.778N2H5+77H5IO63.29, 6.70, 15.078H2N2O234(see above!)H2N2O2-34H4V6O171.9678H2OsO534H2NSO3H1.080H2O-1.3

7 .99* 7.05 1 1.0 1 2.1 H 3O+ * Indicates a thermodynamic value.

Pb(OH)26

.48 (10.92)4 (78) Provided by the ACS, Organic Division Updated 4/7/2022

Page 2

PHOSPHATES AND PHOSPHONATES

CF3-1.16, 3.93 57

CCl

3-1.63, 4.81 57

Phosphates

NH3+CH2-2.35, 5.9 57CompoundpKRef.(-OOCCH2)2NH+CH2---, 5.5757Phosphate1.97, 6.82, 12.555CHCl2-1.14, 5.61 57Glyceric acid 2-phosphate 3.6, 7.153CH2CI-1.40, 6.30 57Enolpyruvic acid3.5, 6.453CH2Br-1.14, 6.52 57Methyl-1.54, 6.31 55(-OOCCH22NH+(CH2)2- --, 6.5457Ethyl-1.60, 6.62 55CH2I-1.30, 6.72 57n-Propyl-1.88,6.6755

NH

3+CH2CH2-2.45, 7.00 57n-Butyl-1.80, 6.84 55

Dimethyl-1.2955C6H5CH=CH-2.00, 7.1 57Di-n-propyl1.5955HOCH2-1.91, 7.15 57Di-n-butyl-1.7255C6H5NH2+(CH2)3-2.1, --57Glucose-3-0.84, 5.67 56C6H5NH(CH2)3---, 7.1757Glucose-4-0.84, 5.67 56Br(CH2)2-2.25, 7.3 57a-glycero-1.40, 6.44 54CH3(CH2)5CH(COO-)---, 7.557b-glycero-1.37, 6.34 54C6H5CH2-2.3, 7.55 573-phosphoglyceric acid1.42, 3.4254

NH

3+(CH2)4)-2.55, 7.55 572-phosphoglyceric acid 1.42, 3.55, 7.1

peroxymonophosphoric acid 4.0569NH3+(CH2)5-2.6, 7.657diphosphoglyceric acid 7.40, 7.99 54NH3+(CH2)10---, 8.0057glyceraldehyde-2.10, 6.75 54-OOC(CH2)10---, 8.2557dioxyacetone-1.77,6.4554

(CH3)3SiCH2-3.22, 8.70 57hexose di-1.52, 6.31 54 fructose-6-0.97, 6.11 54C6H5CH2-3.3, 8.457 glucose-6-0.94, 6.11 54(C6H5)SC-3.85, 9.00 57 glucose-1-1.10, 6.13 54

adenylic acid3.8?, 6.2?54Arylphosphonic acidsinosinic acid2.4?, 6.4?542X-RC6H3PO3H2ADP2 strong, 6.654X RATP3 strong, 6.654Cl 4-O2N 1.12, 6.1457 pyrophosphoric acid0.9, 2.0, 6.6, 9.454Br 5-O2N(a), 6.1457phosphopyruvic acid3.5, 6.38 54Cl5-Cl(a), 6.6357creatine phosphate2.7, 4.554Cl H1.63, 6.98 57arginine phosphate2.8, 4.5, 9.6, 11.254Br H1.64, 7.00 57arginine2.02, 9.0, 12.554Br5-CH31.81, 7.15 57amino phosphate(-0.9), 2.8, 8.254Cl4-NH2--, 7.3357trimetaphosphate2.0577CH3O 4-O2N 1.53, 6.9657

CH

3O H2.16, 7.77 57PhosphonatesCH3O 4-O2N--, 8.2257H2O3P(CH2)4PO3H2 <2, 2.75, 7.54, 8.3857HO 4-O2N 1.22, 5.3957 H2O3P(CH2)3PO3H2 <2, 2.65, 7.34, 8.3557O2N H1.45, 6.74 57H2O3PCH2CH(CH3)PO3H2 <2, 2.6, 7.00, 9.2757F H1.64, 6.80 57H2O3PCH2PO3H2 <2, 2.57, 6.87, 10.3357IH1.74, 7.06 57Methyl-2.3557NH2H--, 7.2957Ethyl-2.4357CH3H 2.10, 7.6857 n-propyl-2.4557C6H5H(a), 8.1357isopropyl-2.55, 7.75 57

HOOC H1.71, 9.17 57n-butyl-2.59, 8.19 57

isobutyl-2.70, 8.43 57 **These values were obtained in 50% ethanol.s-butyl-2.74, 8.48 57 (a) The compounds were not sufficiently soluble.t-butyl-2.79, 8.88 57

For graphical

plots of a large number of substituted phosphorus compounds see 83.neopentyl-2.84, 8.65 57

1,1 Dimethylpropyl-2.88, 8.96 57n-hexyl-2.6, 7.957triphosphate8.90, 6.26, 2.3077n-dodecyl---, 8.2557tetrametaphosphate2.7477CH3(CH2)5CH(COOH)- 1, --57Provided by the ACS, Organic Division Updated 4/7/2022

Page 3

fluorophosphate0.55, 4.856Acetic acids, substituted

Phosphonates (Ref. 2)H-4.76*20

X-H -H-NH 3+-NH3+O2N-1.68*20

X(CH2)PO3H22.35 7.11.85 5.35(CH3)3N+- 1.83*20X(CH2)2PO3H22.45 7.852.45 7.00(CH3)2NH+- 1.95*20X(CH2)4PO3H22.55 7.55CH3NH2+- 2.16*20X(CH2)5PO3 H22.6 7.65NH3+-2.31*20X(CH2)6PO2H22.6 7.9CH3SO2-2.36*20X(CH2)10PO2H28.00NC-2.43*20Phosphines in acetonitrile, see ref. 89.C6H5SO2-2.4420

HO

2C2.83*20CARBOXYLIC ACIDS

AliphaticC6H5SO-2.6620

CompoundpKRef.F-2.6620Acetoacetic 3.586Cl-2.86*20Acetopyruvic 2.61, 7.85 (enol)6 Br-2.8620Aconitic, trans-2.80, 4.46 6Cl2-1.2920Betaine1.846F2-1.2420Citric3.09, 4.75, 5.41 6Br3-0.6620Crotonic4.696Cl3-0.6520Dihydroxyfumaric 1.146F3-0.23 (-0.26) (2) 20Dethylenediamine- 2.00, 2.676 HONC43.0120tetraacetic6.16, 10.26F3C-3.07*20Formic3.77*2N3-3.0320Fumaric3.03, 4.54 6I-3.1220Glyceric3.556C6H5O-3.1220Glycollic3.826C2H5O2C-3.3520Glyoxylic3.326C6H5S-3.52*20Homogentistic 4.406CH3O-3.5320a-keto-b-methyl valeric 2.36

NCS-3.5820Lactic3.866CH3CO-3.58*20Maleic1.93, 6.58 6

Malic3.40, 5.2 6C2H5O-3.6020

Oxaloacetic (trans-enol) 2.56 6n-C3H7O3.6520+(cis-enol) 2.15, 4.066 n-C4H9O3.6620Protocatechuic 4.486sec.-C4H9O- 3.6720Pyruvic2.506HS-3.67*20Tartaric +2.99, 4.40 6i-C3H7O-3.69*20+ or -2.89, 4.40 6CH3S-3.72*20meso3.22, 4.85 6i-C3H7S-3.72*20Vinylacetic4.426C6H5CH2S- 3.73*20

C

2H5S-3.74*20

n-C

3H7S-3.77*20

n-C

4H9S-3.81*20

HO-3.83*20

ÐO3S-4.0520

(C

6H5)3CS- 4.30*20

C

6H5-4.31*20

CH

2-CH-4.35*20

* Indicates thermodynamic values. Provided by the ACS, Organic Division Updated 4/7/2022

Page 4

Unsaturated acids (25°)

CompoundpK ref.CompoundpK ref.

trans-CH

3-CH=CHCO2H 4.69*20 H-CH2CH2CO2H4.88* 2

cis-CH

3-CH=CHCO2H 4.44*2 H-CH=CHCO2H4.25* 2

C

6H5-CH2CH2CO2H 4.66*2 C6H5CH2CH2CO2H 4.66*2

trans-C

6H5-CH=CHCO2H 4.44*2 C6H5CH=CHCO2H** 4.44*2

m-CH

3OC6H4CH2CH2CO2H 4.65*

2C

6H5CH2CH2CO2H 4.66*2

C

6H5CH=CHCO2H** 4.442

m-CH

3OC6H4CH=CHCO2H 4.38*2 m-ClC6H4CH=CHCO2H** 4.29*2

m-ClC

6H4CH2CH2CO2H 4.58*2

Unsaturated acids,

Cis- and Trans-C CR

2H R

1CO2HC CR

2R1 H

CO2HCis-AcidTrans-Acid

R1R2cis-acidtrans-acid Ref.

H-H- 4.25*4.25*2

CH

3-H- 4.44*4.69*2

Cl-H- 3.323.652

C

6H5-H- 3.88*4.44*2

ClC

6H4H- 3.914.412

6-BrC

6H4H- 4.024.412

CH

3-CH3- 4.305.022

C

6H5-H- 5.26***5.58***2

2,4,6-(CH

3)3C6H2- H-6.12*** 5.70***2

C

6H5-CH3- 4.98***5.98***2

Dicarboxylic acids, unsaturated*

Maleic1.92, 6.23 2Alicyclic Dicarboxylic acids

Citraconic (Dimethylmaleic acid)

2.29, 6.15 2cis-Caronic(1,1-dimethylcyclopropane-23-dicarboxylic acid2.34*, 8.31* 2Acetylenedicarboxylic1.73, 4.40 2

D

1-tetrahydrophthalic 3.01, 5.342 1,2-trans-cyclopropanedicarboxylic

3.65*, 5.13* 2Bromomaleic1.45, 4.62 2trans-caronic 3.82*, 5.32*2 Bromofumaric 1.46, 3.572 1,2-cis-cyclopropane-dicarboxylic

3.33*, 6.47* 2Chlorofumaric 1.78, 3.812 Fumaric3.02, 4.38 2

Mesaconic (Dimethylfumaric acid)**trans3.09, 4.75 2***in 40% acetonePhthalic2.95, 5.41 2*thermodynamicItaconic (1-Propene-2-3-dicarboxylic acid)

3.85, 5.45 2

Chloromaleic1.72, 3.86 2Provided by the ACS, Organic Division Updated 4/7/2022

Page 5

Aliphatic

Alicyclic Dicarboxylic acids

CompoundpKRef CompoundpKRef

dicarboxylic3.65, 5.13 2dicarboxylic1.94, 3.92 2 trans-Ethyleneoxide-1,3-cis-Cyclobutane- dicarboxylic1.93, 3.25 2dicarboxylic4.03, 5.31 2

1,3-trans -Cyclobutanedi-1,2-cis-Cyclopentane-

carboxylic3.81, 5.28 2dicarboxylic4.37, 6.51 2 dicarboxylic3.89, 5.91 2dicarboxylic4.23, 5.53 2 dicarboxylic4.40, 5.45 2dicarboxylic4.34, 6.76 2

1,2-trans-Cyclohexane-1,3 -cis-Cyclohexane-

dicarboxylic4.18, 5.93 2dicarboxylic4.10, 5.46 2 dicarboxylic4.31, 5.73 2di-carboxylic4.44, 5.79 2

1,4-trans-Cyclohexane-

dicarboxylic4.18, 5.42 2

Dicarboxylic acids*

oxalic1.23, 4.19 2Succinic4.19, 5.48 2

Malonic2.83, 5.69 2 O-O'-Dimethyl-3.77, 5.94 2

Methyl-3.05, 5.76 2 (high melting)

Ethyl-2.99, 5.83 2 O-O'-Dimethyl-3.94, 6.20 2

n-propyl3.00, 5.84 2 (low melting) i-propyl-2.94, 5.88 2O,O'-Diethyl-3.63, 6.46 2

Dimethyl-3.17, 6.06 2 (high melting)

Methylethyl-2.86, 6.41 2O,O'-Diethyl-3.51, 6.60 2

Diethyl-2.21, 7.29 2 (low melting)

Ethyl-n-propyl-2.15, 7.43 2Tetramethyl-3.50, 7.28 2

Di-n-propyl-2.07, 7.51 2

Glutaric4.34, 5.42 2Adipic4.42, 5.41 2

B-Methyl4.25, 6.22 2Pimelic4.48, 5.42 2

B-Ethyl4.29, 6.33 2Suberic4.52, 5.40 2

B-n-Propyl4.31, 6.392Azelaic4.55, 5.41 2

B,B-Dimethyl-3.70, 6.29 2DL-1:2-Dichlorosuccinic1.68, 3.1820 B,B-Methylethyl-3.62, 6.70 2meso-1:2-Dichlorosuccinic 1.74, 3.2420 B,B-Diethyl-3.62, 7.12 2DL-1:2-Dibromosuccinic1.48, ----20 B,B-Di-n-propyl3.69, 7.31 2meso-1:2-Dibromosuccinic 1.42, 2.9720 D-Tartaric3.03, 4.4520 DL-1:2-Dimethylsuccinic3.93, 6.0020 DL-Tartaric3.03, ----20meso-1:2-Dimethylsuccinic 3.77, 5.3620 meso-Tartaric3.29, 4.9220 *All are thermodynamic values

AliphaticHO-6.332

Bicyclo[2.2.2]octane-1-carboxylic acids, 4-

substitutedBr-6.082

Lysergic acid, etc.

H-6.752ergometrine6.8, -- 2

C

2H5O2C-6.312Dihydroergometrine7.4, -- 2

b-dihydrolysergol 8.2, --2 NC-5.902Provided by the ACS, Organic Division Updated 4/7/2022

Page 6

Lysergic acid7.8, 3.3 2C6H5O- 3.53*3.95* 4.52*

a-dihydrolysergic 8.3, 3.62 CH3-3.91* 4.24*4.34*

ergometrinine7.3, -- 2(CH3)2CH-4.35*a-dihydrolysergol 8.3, --2 (CH3)3N+- 1.373.45 3.436-methylergoline8.85, -- 2NC-3.60* 3.55*isolysergic acid8.4, 3.4 2HO2C* 2.95*3.54 3.51g-dihydrolysergic 8.6, 3.62 F3C-3.79

HO-2.98* 4.08*4.58*

I-2.85* 3.86*Hydroxycyclohexanecarboxylic acidsCl-2.94* 3.83*3.99* Cyclohexanecarboxylic 4.902(CH3)3Si-4.24* 4.27*cis-1,24.80 2C2H5O- 4.21*4.17* 4.45*cis-1,34.60 2i-C3H7O- 4.24*4.15* 4.68*cis-1,44.84 2n-C5H11O-4.55*trans-1,24.68 2C6H5- 3.46*trans-1,34.82 2CH3CH2- 3.774.35*trans-1,44.68 2(CH3)3C- 3.464.28 4.40*

ÐHO3P- 3.784.03 3.95Aromatic

benzene-CO

3H4.20* 2ÐO3S-4.15 4.11

Anthracene-1-COOH 3.692 H2N-4.98 4.794.92 Anthracene-9-COOH 3.652 (CH3)2N- 8.425.10 5.03naphthalene-2-COOH 4.172 ÐHO3As-4.22Naphthalene-1-COOH 3.692 ÐO2C- 5.41**4.60 4.82

CH

3NH- 5.35.10 5.04Substituted benzoic acids (ref. 2)COOH*thermodynamicfor complex chelating agents, see also ref. 84.see also page 9a for more carboxylic acids.Benzoic acid om p

Ortho-substituted benzoic acids

H-4.20* 4.21*Benzoic acid pKRef.O2N-2.17* 3.45*3.44 2-CH3-3.91** 2CH3CO-2-t-C4H9-3.462CH3SO2-3.64* 3.52*2,6-(CH3)2- 3.212CH3S-2,3,4,6-(CH3)4- 4.002HS-2,3,5,6-(CH3)4- 3.522Br-2.85* 3.81*4.00* 2-C2H5-3.772F-3.27* 3.87*4.14*

CH

3O- 4.09*4.09* 4.47*2-C6H5-3.46** 2

n-C

3H7O- 4.24*4.20* 4.46*2,4,6-(CH3)3- 3.432

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