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ClCH2CO2 anion


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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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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

ClCH2CO2 anion + Water = (ClCH2CO2 anion bullet Water)

By formula: C2H2ClO2- + H2O = (C2H2ClO2- bullet H2O)

Bond type: Hydrogen bond (negative ion to hydride)

Quantity Value Units Method Reference Comment
Deltar14.7 ± 1.5kcal/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. «DELTA»Saff approx. 24 cal/mol-K; B
Quantity Value Units Method Reference Comment
Deltar7.70 ± 0.30kcal/molTDAsBlades, Klassen, et al., 1995gas phase; T: 293 K. «DELTA»Saff approx. 24 cal/mol-K; B,M

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]

Blades, Klassen, et al., 1995
Blades, A.T.; Klassen, J.S.; Kebarle, P., Free Energies of Hydration in the Gas Phase on the Anions of Some Oxo Acids of C, N, S, P, Cl and I, J. Am. Chem. Soc., 1995, 117, 42, 10563, https://doi.org/10.1021/ja00147a019 . [all data]


Notes

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