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Acetic acid, chloro-

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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

ClCH2CO2 anion + Hydrogen cation = Acetic acid, chloro-

By formula: C2H2ClO2- + H+ = C2H3ClO2

Quantity Value Units Method Reference Comment
Deltar1408. ± 9.2kJ/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Deltar1407. ± 9.2kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1407. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Deltar1377. ± 8.4kJ/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Deltar1376. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1376. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B

Chlorine anion + Acetic acid, chloro- = (Chlorine anion bullet Acetic acid, chloro-)

By formula: Cl- + C2H3ClO2 = (Cl- bullet C2H3ClO2)

Quantity Value Units Method Reference Comment
Deltar59.0 ± 8.4kJ/molIMRELarson and McMahon, 1985gas phase; B
Quantity Value Units Method Reference Comment
Deltar33. ± 8.4kJ/molIMRELarson and McMahon, 1985gas phase; B

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

By formula: H2O + C3H5ClO2 = CH4O + C2H3ClO2

Quantity Value Units Method Reference Comment
Deltar-57.3 ± 2.9kJ/molEqkGuthrie and Cullimore, 1980liquid phase; Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol; ALS

Water + Acetyl chloride, chloro- = Hydrogen chloride + Acetic acid, chloro-

By formula: H2O + C2H2Cl2O = HCl + C2H3ClO2

Quantity Value Units Method Reference Comment
Deltar-93.51kJ/molCmPritchard and Skinner, 1950liquid phase; Heat of hydrolysis at 298 K; 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]

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Larson and McMahon, 1985
Larson, J.W.; McMahon, T.B., Fluoride and chloride affinities of the main group oxides, fluorides, oxofluorides, and alkyls. Quantitative scales of lewis acidities from ICR halide exchange equilibria, J. Am. Chem. Soc., 1985, 107, 766. [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]

Pritchard and Skinner, 1950
Pritchard, H.O.; Skinner, H.A., The heats of hydrolysis of the chloro-substituted acetyl chlorides, J. Chem. Soc., 1950, 272-276. [all data]


Notes

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