A theoretical investigation of the enol content of acetic acid and the acetate ion in aqueous solution

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Abstract

Ab initio molecular orbital calculations and statistical Monte Carlo simulations employing a combined quantum and molecular mechanical potential were used to determine the enol contents of acetic acid and the acetate ion in aqueous solution. A pKE of 19.3 ± 0.3 was predicted for the keto-enol equilibrium of acetic acid, and 21.8 ± 0.8 for the acetate ion in water. The results are found to be in good accord with Guthrie's calculations based on disproportionation reactions and kinetic data. Combining with the experimental pKa value of acetic acid, we obtained pKKa = 26.6 for ionization of acetic acid as a carbon acid in water, and pKEa = 7.3 for ionization of the enol of acetic acid.

Original languageEnglish (US)
Pages (from-to)203-208
Number of pages6
JournalJournal of Molecular Structure: THEOCHEM
Volume370
Issue number2-3
DOIs
StatePublished - Oct 30 1996

Bibliographical note

Funding Information:
This work was supportedb y the National Science Foundation. Discussion with Professor J. P. Richard was also helpful.

Copyright:
Copyright 2018 Elsevier B.V., All rights reserved.

Keywords

  • Acetic acid
  • Combined QM/MM simulations
  • Enol
  • Enolate
  • Keto-enol equilibrium

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