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Acetic acid, chloro-

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Condensed phase 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:
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltacsolid-174. ± 1.kcal/molCcbSmith, Bjellerup, et al., 1953ALS
Deltacsolid-173.7kcal/molCcbSchjanberg, 1935ALS

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
43.00321.05Urazovskii and Sidorov, 1950T = 47 to 65°C. Value is unsmoothed experimental datum. Maxima at 50.7, 56.9, and 61.2°C.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
34.4288. - 318.Pickering, 1895T = 288 to 349 K.; DH

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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

ClCH2CO2 anion + Hydrogen cation = Acetic acid, chloro-

By formula: C2H2ClO2- + H+ = C2H3ClO2

Quantity Value Units Method Reference Comment
Deltar336.5 ± 2.2kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Deltar336.2 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar336.3 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Deltar329.0 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Deltar328.8 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar328.8 ± 2.0kcal/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
Deltar14.1 ± 2.0kcal/molIMRELarson and McMahon, 1985gas phase; B
Quantity Value Units Method Reference Comment
Deltar7.8 ± 2.0kcal/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-13.70 ± 0.70kcal/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-22.35kcal/molCmPritchard and Skinner, 1950liquid phase; Heat of hydrolysis at 298 K; ALS

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

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

Smith, Bjellerup, et al., 1953
Smith, L.; Bjellerup, L.; Krook, S.; Westermark, H., Heats of combustion of organic chloro compounds determined by the "quartz wool" method, Acta Chem. Scand., 1953, 7, 65. [all data]

Schjanberg, 1935
Schjanberg, E., Die Verbrennungswarmen und die Refraktionsdaten einiger chlorsubstituierter Fettsauren und Ester., Z. Phys. Chem. Abt. A, 1935, 172, 197-233. [all data]

Urazovskii and Sidorov, 1950
Urazovskii, S.S.; Sidorov, I.A., Concerning singularities in the temperature dependence of the specific heat of liquids and the nature of phase transitions of the second kind, Doklady Akad. Nauk, 1950, SSSR 70, 859-862. [all data]

Pickering, 1895
Pickering, S.U., A comparison of some properties of acetic acid and its chloro- and bromo-derivatives, J. Chem. Soc., 1895, 67, 664-684. [all data]

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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