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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
Deltacliquid-149. ± 1.kcal/molCcbSmith, Bjellerup, et al., 1953ALS
Deltacliquid-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

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

C2HCl2O2- + Hydrogen cation = Acetic acid, dichloro-

By formula: C2HCl2O2- + H+ = C2H2Cl2O2

Quantity Value Units Method Reference Comment
Deltar328.4 ± 2.1kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Deltar328.4 ± 2.6kcal/molG+TSCumming and Kebarle, 1978gas phase; B
Deltar327.3 ± 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
Deltar321.9 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B
Deltar321.9 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; B
Deltar320.8 ± 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
Deltar-25.73kcal/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]

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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