TY - JOUR
T1 - A theoretical investigation of the enol content of acetic acid and the acetate ion in aqueous solution
AU - Gao, Jiali
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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U2 - 10.1016/S0166-1280(96)04702-1
DO - 10.1016/S0166-1280(96)04702-1
M3 - Article
AN - SCOPUS:0001678587
VL - 370
SP - 203
EP - 208
JO - Computational and Theoretical Chemistry
JF - Computational and Theoretical Chemistry
SN - 2210-271X
IS - 2-3
ER -