Benzoic acid, 2-chloro-

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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas-72.7 ± 0.2kcal/molCcrSabbah and Rojas Aguilar, 1995HCl(1:600 H2O)

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

C7H4ClO2- + Hydrogen cation = Benzoic acid, 2-chloro-

By formula: C7H4ClO2- + H+ = C7H5ClO2

Quantity Value Units Method Reference Comment
Δr335.1 ± 2.1kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr328.2 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

Benzoyl chloride, 2-chloro- + Water = Benzoic acid, 2-chloro- + Hydrogen chloride

By formula: C7H4Cl2O + H2O = C7H5ClO2 + HCl

Quantity Value Units Method Reference Comment
Δr-9.50 ± 0.06kcal/molCmMoselhy and Pritchard, 1975liquid phase; solvent: Diphenyl-ether; Heat of hydrolysis; ALS

Gas phase ion energetics 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 by: John E. Bartmess

De-protonation reactions

C7H4ClO2- + Hydrogen cation = Benzoic acid, 2-chloro-

By formula: C7H4ClO2- + H+ = C7H5ClO2

Quantity Value Units Method Reference Comment
Δr335.1 ± 2.1kcal/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr328.2 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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

Sabbah and Rojas Aguilar, 1995
Sabbah, R.; Rojas Aguilar, A., Etude thermodynamique des trois isomeres de l'acide chlorobenzoique. Partie II, Can. J. Chem., 1995, 73, 1538-1545. [all data]

Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B., Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria, J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032 . [all data]

Moselhy and Pritchard, 1975
Moselhy, G.M.; Pritchard, H.O., The thermochemistry of the chloro-benzoyl chlorides, J. Chem. Thermodyn., 1975, 7, 977-982. [all data]


Notes

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