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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
Deltafgas-72.7 ± 0.2kcal/molCcrSabbah and Rojas Aguilar, 1995HCl(1:600 H2O)

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
Deltafsolid-96.8 ± 0.1kcal/molCcrSabbah and Rojas Aguilar, 1995HCl(1:600 H2O); ALS
Deltafsolid-96.76 ± 0.18kcal/molCcrJohnson and Prosen, 1974ALS
Quantity Value Units Method Reference Comment
Deltacsolid-737.992 ± 0.060kcal/molCcrSabbah and Rojas Aguilar, 1995HCl(1:600 H2O); ALS
Deltacsolid-734.5 ± 1.1kcal/molCcbHoldiness, 1983ALS
Deltacsolid-738.03 ± 0.16kcal/molCcrJohnson and Prosen, 1974ALS
Deltacsolid-739.5 ± 2.0kcal/molCcbSmith, Bjellerup, et al., 1953Reanalyzed by Cox and Pilcher, 1970, Original value = -739. ± 2. kcal/mol; ALS

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
39.01298.Andrews, Lynn, et al., 1926T = 22 to 200 C.; 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

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

By formula: C7H4ClO2- + H+ = C7H5ClO2

Quantity Value Units Method Reference Comment
Deltar335.1 ± 2.1kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar328.2 ± 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
Deltar-9.50 ± 0.06kcal/molCmMoselhy and Pritchard, 1975liquid phase; solvent: Diphenyl-ether; Heat of hydrolysis; ALS

References

Go To: Top, Gas phase thermochemistry data, 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.

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]

Johnson and Prosen, 1974
Johnson, W.H.; Prosen, E.J., The enthalpies of combustion and formation of the mono-chlorobenzoic acids, J. Res. NBS, 1974, 78, 683-689. [all data]

Holdiness, 1983
Holdiness, M.R., Heats of atomization and resonance energy of some ortho-substituted benzoic acids, Thermochim. Acta, 1983, 71, 257-263. [all data]

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]

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

Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J., The heat capacities and heat of crystallization of some isomeric aromatic compounds, J. Am. Chem. Soc., 1926, 48, 1274-1287. [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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