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Section: 5 | Dissociation Constants of Organic Acids and Bases |
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The recommended form of citation is:
John R. Rumble, ed., CRC Handbook of Chemistry and Physics, 103rd Edition (Internet Version 2022), CRC Press/Taylor & Francis, Boca Raton, FL.
If a specific table is cited, use the format: "Physical Constants of Organic Compounds," in CRC Handbook of Chemistry and Physics, 103rd Edition (Internet Version 2022), John R. Rumble, ed., CRC Press/Taylor & Francis, Boca Raton, FL.

DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES

This table lists the dissociation (ionization) constants of over 1070 organic acids, bases, and amphoteric compounds. All data apply to dilute aqueous solutions and are presented as values of pKa, which is defined as the negative of the logarithm of the equilibrium constant Ka for the reaction

HA ⇌ H+ + A-

i.e.,

Ka = [H+][A-]/[HA]

where [H+], etc., represent the concentrations of the respective species in mol/L. It follows that pKa = pH + log[HA] – log[A-], so that a solution with 50% dissociation has pH equal to the pKa of the acid.

Data for bases are presented as pKa values for the conjugate acid, i.e., for the reaction

BH+ ⇌ H+ + B

In older literature, an ionization constant Kb was used for the reaction B + H2O ⇌ BH+ + OH- . This is related to Ka by

pKa + pKb = pKwater = 14.00 (at 25 °C)

Compounds are listed alphabetically by name.

References

  1. Perrin, D. D., Dissociation Constants of Organic Bases in Aqueous Solution, Butterworths, London, 1965; Supplement, 1972.
  2. Serjeant, E. P., and Dempsey, B., Ionization Constants of Organic Acids in Aqueous Solution, Pergamon, Oxford, 1979.
  3. Albert, A., “Ionization Constants of Heterocyclic Substances”, in Katritzky, A. R., Ed., Physical Methods in Heterocyclic Chemistry, Academic Press, New York, 1963.
  4. Sober, H. A., Ed., CRC Handbook of Biochemistry, CRC Press, Boca Raton, FL, 1968.
  5. Perrin, D. D., Dempsey, B., and Serjeant, E. P., pKa Prediction for Organic Acids and Bases, Chapman and Hall, London, 1981. [https://doi.org/10.1007/978-94-009-5883-8]
  6. Albert, A., and Serjeant, E. P., The Determination of Ionization Constants, Third Edition, Chapman and Hall, London, 1984. [https://doi.org/10.1007/978-94-009-5548-6]
  7. O’Neil, M. J., Ed., The Merck Index, 14th Edition, Merck & Co., Whitehouse Station, NJ, 2006.
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Acid Dissociation Constants (as Negative Logarithms) of Organic Acids and Bases at Specified Temperatures



NameSynonymMol. form.CAS Reg. No.Mol. wt.Stept/ºCpKa
Continued on next page...
AcetaldehydeEthanalC2H4O75-07-044.0522513.57
AcetamideEthanamideC2H5NO60-35-559.0672515.1
AcetanilideN-PhenylacetamideC8H9NO103-84-4135.163250.5
AcetazolamideN-[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]acetamideC4H6N4O3S259-66-5222.2467.2
Acetic acidEthanoic acidC2H4O264-19-760.052254.756
Acetoacetic acidC4H6O3541-50-4102.089253.6
Acetohydroxamic acidN-HydroxyacetamideC2H5NO2546-88-375.0678.70
N-AcetylglycineAceturic acidC4H7NO3543-24-8117.104253.67
2-(Acetyloxy)benzoic acidAcetylsalicylic acidC9H8O450-78-2180.158253.48
AconineC25H41NO9509-20-6499.5969.52
AconitineC34H47NO11302-27-2645.7375.88
9-AcridinamineAminacrineC13H10N290-45-9194.231209.99
AcridineDibenzo[b,e]pyridineC13H9N260-94-6179.217205.58
3,6-AcridinediamineProflavineC13H11N392-62-6209.246209.65
Acrylic acid2-Propenoic acidC3H4O279-10-772.063254.25
Adenine1H-Purin-6-amineC5H5N573-24-5135.12814.3
Adenine1H-Purin-6-amineC5H5N573-24-5135.12829.83
Adenosineβ-D-Ribofuranoside, adenine-9C10H13N5O458-61-7267.2421253.6
Adenosineβ-D-Ribofuranoside, adenine-9C10H13N5O458-61-7267.24222512.4

  • aApproximate value.


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