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)

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
Δfsolid-96.8 ± 0.1kcal/molCcrSabbah and Rojas Aguilar, 1995HCl(1:600 H2O); ALS
Δfsolid-96.76 ± 0.18kcal/molCcrJohnson and Prosen, 1974ALS
Quantity Value Units Method Reference Comment
Δcsolid-737.992 ± 0.060kcal/molCcrSabbah and Rojas Aguilar, 1995HCl(1:600 H2O); ALS
Δcsolid-734.5 ± 1.1kcal/molCcbHoldiness, 1983ALS
Δcsolid-738.03 ± 0.16kcal/molCcrJohnson and Prosen, 1974ALS
Δcsolid-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

Phase change 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
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
Tfus413.4KN/AAndrews, Lynn, et al., 1926, 2Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Δsub25.4 ± 0.1kcal/molMERibeiro da Silva, Fonseca, et al., 2005Based on data from 320. to 339. K.; AC
Δsub24.1 ± 0.1kcal/molCSabbah and Aguilar, 1995AC
Δsub24.1 ± 0.1kcal/molCSabbah and Rojas Aguilar, 1995HCl(1:600 H2O); ALS

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
25.10 ± 0.1330.MERibeiro da Silva, Fonseca, et al., 2005Based on data from 320. to 339. K.; AC
19.0 ± 0.4333.VWolf and Weghofer, 1938ALS

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
6.2835414.10N/ASabbath and Hirtz, 1991DH
6.035414.DSCRibeiro da Silva, Fonseca, et al., 2005AC
6.150413.4N/AAcree, 1991AC
6.29414.N/ASabbah and Hirtz, 1991AC
6.1496413.4N/AAndrews, Lynn, et al., 1926DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
14.9413.4Andrews, Lynn, et al., 1926DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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, Condensed phase thermochemistry data, Phase change 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]

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]

Andrews, Lynn, et al., 1926, 2
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. [all data]

Ribeiro da Silva, Fonseca, et al., 2005
Ribeiro da Silva, Manuel A.V.; Fonseca, José M.S.; Carvalho, Rui P.B.M.; Monte, Manuel J.S., Thermodynamic study of the sublimation of six halobenzoic acids, The Journal of Chemical Thermodynamics, 2005, 37, 3, 271-279, https://doi.org/10.1016/j.jct.2004.09.005 . [all data]

Sabbah and Aguilar, 1995
Sabbah, Raphaël; Aguilar, Aaron Rojas, Étude thermodynamique des trois isomères de l'acide chlorobenzoïque. Partie II, Can. J. Chem., 1995, 73, 9, 1538-1545, https://doi.org/10.1139/v95-191 . [all data]

Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H., Uber sublimationswarmen, Z. Phys. Chem., 1938, 39, 194-208. [all data]

Sabbath and Hirtz, 1991
Sabbath, R.; Hirtz, H., Etude thermodynamique des trois acides chlorobenzoiques, 1991, Bull. [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Sabbah and Hirtz, 1991
Sabbah, R.; Hirtz, H., Thermodynamic study of chlorobenzoic acids, Bull. Soc. Chim. Fr., 1991, 26. [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]


Notes

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