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

Jiali Gao

doi:10.1016/S0166-1280(96)04702-1

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

Jiali Gao

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

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 pK_E 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 pK_a value of acetic acid, we obtained pK^K_a = 26.6 for ionization of acetic acid as a carbon acid in water, and pK^E_a = 7.3 for ionization of the enol of acetic acid.

Original language	English (US)
Pages (from-to)	203-208
Number of pages	6
Journal	Journal of Molecular Structure: THEOCHEM
Volume	370
Issue number	2-3
DOIs	https://doi.org/10.1016/S0166-1280(96)04702-1
State	Published - 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.

Keywords

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

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10.1016/S0166-1280(96)04702-1

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title = "A theoretical investigation of the enol content of acetic acid and the acetate ion in aqueous solution",

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.",

keywords = "Acetic acid, Combined QM/MM simulations, Enol, Enolate, Keto-enol equilibrium",

author = "Jiali Gao",

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

year = "1996",

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doi = "10.1016/S0166-1280(96)04702-1",

language = "English (US)",

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journal = "Computational and Theoretical Chemistry",

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TY - JOUR

T1 - A theoretical investigation of the enol content of acetic acid and the acetate ion in aqueous solution

AU - Gao, Jiali

N1 - Funding Information: This work was supportedb y the National Science Foundation. Discussion with Professor J. P. Richard was also helpful.

PY - 1996/10/30

Y1 - 1996/10/30

N2 - 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.

AB - 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.

KW - Acetic acid

KW - Combined QM/MM simulations

KW - Enol

KW - Enolate

KW - Keto-enol equilibrium

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DO - 10.1016/S0166-1280(96)04702-1

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SP - 203

EP - 208

JO - Computational and Theoretical Chemistry

JF - Computational and Theoretical Chemistry

SN - 2210-271X

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

Abstract

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