Benzoic acid, 2-chloro-
- Formula: C7H5ClO2
- Molecular weight: 156.566
- IUPAC Standard InChIKey: IKCLCGXPQILATA-UHFFFAOYSA-N
- CAS Registry Number: 118-91-2
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Benzoic acid, o-chloro-; o-Chlorobenzoic acid; 2-Chlorobenzoic acid; 2-CBA; Chlorobenzoic acid; Kyselina o-chlorbenzoova
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Gas phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, References, Notes
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 |
---|---|---|---|---|---|
ΔfH°gas | -72.7 ± 0.2 | kcal/mol | Ccr | Sabbah and Rojas Aguilar, 1995 | HCl(1:600 H2O) |
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 |
---|---|---|---|---|---|
Tfus | 413.4 | K | N/A | Andrews, Lynn, et al., 1926 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 25.4 ± 0.1 | kcal/mol | ME | Ribeiro da Silva, Fonseca, et al., 2005 | Based on data from 320. to 339. K.; AC |
ΔsubH° | 24.1 ± 0.1 | kcal/mol | C | Sabbah and Aguilar, 1995 | AC |
ΔsubH° | 24.1 ± 0.1 | kcal/mol | C | Sabbah and Rojas Aguilar, 1995 | HCl(1:600 H2O); ALS |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
25.10 ± 0.1 | 330. | ME | Ribeiro da Silva, Fonseca, et al., 2005 | Based on data from 320. to 339. K.; AC |
19.0 ± 0.4 | 333. | V | Wolf and Weghofer, 1938 | ALS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
6.2835 | 414.10 | N/A | Sabbath and Hirtz, 1991 | DH |
6.035 | 414. | DSC | Ribeiro da Silva, Fonseca, et al., 2005 | AC |
6.150 | 413.4 | N/A | Acree, 1991 | AC |
6.29 | 414. | N/A | Sabbah and Hirtz, 1991 | AC |
6.1496 | 413.4 | N/A | Andrews, Lynn, et al., 1926, 2 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
14.9 | 413.4 | Andrews, Lynn, et al., 1926, 2 | DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change data, References, Notes
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- + =
By formula: C7H4ClO2- + H+ = C7H5ClO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 335.1 ± 2.1 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 328.2 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas phase |
References
Go To: Top, Gas 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]
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. [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]
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, 1274-1287. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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