Benzoic acid, 2-chloro-
- Formula: C7H5ClO2
- Molecular weight: 156.566
- IUPAC Standard InChI: InChI=1S/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)
- 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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Condensed phase thermochemistry data
Go To: Top, 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 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 |
|---|---|---|---|---|---|
| ΔfH°solid | -96.8 ± 0.1 | kcal/mol | Ccr | Sabbah and Rojas Aguilar, 1995 | HCl(1:600 H2O); ALS |
| ΔfH°solid | -96.76 ± 0.18 | kcal/mol | Ccr | Johnson and Prosen, 1974 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -737.992 ± 0.060 | kcal/mol | Ccr | Sabbah and Rojas Aguilar, 1995 | HCl(1:600 H2O); ALS |
| ΔcH°solid | -734.5 ± 1.1 | kcal/mol | Ccb | Holdiness, 1983 | ALS |
| ΔcH°solid | -738.03 ± 0.16 | kcal/mol | Ccr | Johnson and Prosen, 1974 | ALS |
| ΔcH°solid | -739.5 ± 2.0 | kcal/mol | Ccb | Smith, Bjellerup, et al., 1953 | Reanalyzed 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 |
|---|---|---|---|
| 39.01 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 200 C.; DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry 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, Condensed phase 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]
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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