Acetic acid, dichloro-

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

Quantity Value Units Method Reference Comment
Δcliquid-149. ± 1.kcal/molCcbSmith, Bjellerup, et al., 1953ALS
Δcliquid-148.1kcal/molCcbSchjanberg, 1935ALS

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
49.5291. - 323.Pickering, 1895T = 253 to 323 K.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
43.571280.31Glasgow and Timmerman, 1961T = -180 to 7°C. Value is unsmoothed experimental datum.; 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

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Individual Reactions

C2HCl2O2- + Hydrogen cation = Acetic acid, dichloro-

By formula: C2HCl2O2- + H+ = C2H2Cl2O2

Quantity Value Units Method Reference Comment
Δr328.4 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Δr328.4 ± 2.6kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Δr327.3 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr321.9 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Δr321.9 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B
Δr320.8 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

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

By formula: H2O + C2HCl3O = HCl + C2H2Cl2O2

Quantity Value Units Method Reference Comment
Δr-25.73kcal/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.

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]

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]

Glasgow and Timmerman, 1961
Glasgow, A.R.; Timmerman, J., Some physical properties of monochloro-, dichloro-, and monobromoacetic acids at 1 atmosphere, Bull. Soc. Chim. Belg., 1961, 70, 599-622. [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]

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]

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]

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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