Acetic acid, methoxy-

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Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

MeOCH2CO2 anion + Hydrogen cation = Acetic acid, methoxy-

By formula: C3H5O3- + H+ = C3H6O3

Quantity Value Units Method Reference Comment
Δr341.9 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Δr342.6 ± 2.1kcal/molG+TSTaft and Topsom, 1987gas phase; B
Quantity Value Units Method Reference Comment
Δr335.3 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Δr336.0 ± 2.0kcal/molIMRETaft and Topsom, 1987gas phase; B

Acetic acid, methoxy-, methyl ester + Water = Acetic acid, methoxy- + Methyl Alcohol

By formula: C4H8O3 + H2O = C3H6O3 + CH4O

Quantity Value Units Method Reference Comment
Δr-15.7 ± 1.4kcal/molEqkGuthrie and Cullimore, 1980liquid phase; ALS

Acetic anhydride + 2Acetic acid, methoxy- = Acetic acid, methoxy-, anhydride + 2Acetic acid

By formula: C4H6O3 + 2C3H6O3 = C6H10O5 + 2C2H4O2

Quantity Value Units Method Reference Comment
Δr0.0kcal/molEqkUtkin, Bogel'fer, et al., 1991liquid phase; NMR; ALS

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Caldwell, Renneboog, et al., 1989
Caldwell, G.; Renneboog, R.; Kebarle, P., Gas Phase Acidities of Aliphatic Carboxylic Acids, Based on Measurements of Proton Transfer Equilibria, Can. J. Chem., 1989, 67, 4, 661, https://doi.org/10.1139/v89-092 . [all data]

Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D., The Nature and Analysis of Substituent Effects, Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Guthrie and Cullimore, 1980
Guthrie, J.P.; Cullimore, P.A., Effect of the acyl substituent on the equilibrium constant for hydration of esters, Can. J. Chem., 1980, 58, 1281-1294. [all data]

Utkin, Bogel'fer, et al., 1991
Utkin, A.Yu.; Bogel'fer, L.Ya.; Chimishkyan, A.L., Reversible reactions in the acidolysis of methyoxyacetic acid by acetic anhydride, Russ. J. Phys. Chem. (Engl. Transl.), 1991, 65, 1049-1059, In original 1974. [all data]


Notes

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