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Benzoic acid

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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
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

benzoate anion + Hydrogen cation = Benzoic acid

By formula: C7H5O2- + H+ = C7H6O2

Quantity Value Units Method Reference Comment
Deltar340.1 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar340.0 ± 2.9kcal/molG+TSCumming and Kebarle, 1978gas phase; Recalculated from data in paper; error in Table vs. ladder; B
Deltar340.2 ± 2.2kcal/molG+TSCaldwell, Renneboog, et al., 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar333.0 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar332.9 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; Recalculated from data in paper; error in Table vs. ladder; B
Deltar333.1 ± 2.0kcal/molIMRECaldwell, Renneboog, et al., 1989gas phase; B

Bromine anion + Benzoic acid = (Bromine anion bullet Benzoic acid)

By formula: Br- + C7H6O2 = (Br- bullet C7H6O2)

Quantity Value Units Method Reference Comment
Deltar18.3 ± 1.8kcal/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
Deltar20.cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar9.8 ± 1.0kcal/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
9.8423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

Water + Benzoyl chloride = Benzoic acid + Hydrogen chloride

By formula: H2O + C7H5ClO = C7H6O2 + HCl

Quantity Value Units Method Reference Comment
Deltar-8.136 ± 0.050kcal/molCmMoselhy and Pritchard, 1975liquid phase; solvent: Diphenyl-ether; see Carson, Pritchard, et al., 1950 and Davies, Dunning, et al., 1972; ALS
Deltar-24.35kcal/molCmCarson, Pritchard, et al., 1950liquid phase; Heat of hydrolysis; ALS

Benzaldehyde + perbenzoic acid = 2Benzoic acid

By formula: C7H6O + C7H6O3 = 2C7H6O2

Quantity Value Units Method Reference Comment
Deltar-75.6 ± 3.0kcal/molCmBriner and Chastonay, 1954liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -75.7 ± 3.0 kcal/mol; ALS

Benzoyl bromide + Water = Hydrogen bromide + Benzoic acid

By formula: C7H5BrO + H2O = HBr + C7H6O2

Quantity Value Units Method Reference Comment
Deltar-27.04kcal/molCmCarson, Pritchard, et al., 1950liquid phase; Heat of hydrolysis; ALS

Benzoyl iodide + Water = Hydrogen iodide + Benzoic acid

By formula: C7H5IO + H2O = HI + C7H6O2

Quantity Value Units Method Reference Comment
Deltar-24.47kcal/molCmCarson, Pritchard, et al., 1950liquid phase; Heat of hydrolysis; ALS

Water + Benzoic acid, methyl ester = Benzoic acid + Methyl Alcohol

By formula: H2O + C8H8O2 = C7H6O2 + CH4O

Quantity Value Units Method Reference Comment
Deltar-17.44 ± 0.45kcal/molEqkGuthrie and Cullimore, 1980liquid phase; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

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

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]

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]

Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P., Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-, J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014 . [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]

Carson, Pritchard, et al., 1950
Carson, A.S.; Pritchard, H.O.; Skinner, H.A., The heats of hydrolysis of the benzoyl halides, J. Chem. Soc., 1950, 656-659. [all data]

Davies, Dunning, et al., 1972
Davies, J.V.; Dunning, B.K.; Pritchard, H.O., The enthalpy of formation of benzoyl chloride, J. Chem. Thermodyn., 1972, 4, 731-737. [all data]

Briner and Chastonay, 1954
Briner, E.; Chastonay, P., Etude thermochemique de l'autoxydation de Valdehyde benzoique, Helv. Chim. Acta, 1954, 238, 539-541. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]


Notes

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