Benzoic acid, 4-chloro-
- Formula: C7H5ClO2
- Molecular weight: 156.566
- IUPAC Standard InChIKey: XRHGYUZYPHTUJZ-UHFFFAOYSA-N
- CAS Registry Number: 74-11-3
- 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, p-chloro-; p-Chlorbenzoic acid; p-Chlorobenzoic acid; Chlorodracylic acid; 4-Chlorobenzoic acid; Acido p-clorobenzoico; p-Carboxychlorobenzene
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Phase change data
Go To: Top, 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:
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 | 511. | K | N/A | Kaluszyner and Reuter, 1953 | Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 512. | K | N/A | Cope and Schmitz, 1950 | Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 512.9 | K | N/A | Cope and Schmitz, 1950 | Uncertainty assigned by TRC = 4. K; TRC |
Tfus | 512.85 | K | N/A | Andrews, Lynn, et al., 1926 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 105.2 ± 0.7 | kJ/mol | ME | Ribeiro da Silva, Fonseca, et al., 2005 | Based on data from 333. to 356. K.; AC |
ΔsubH° | 102.5 ± 0.4 | kJ/mol | C | Sabbah and Aguilar, 1995 | AC |
ΔsubH° | 102.5 ± 0.4 | kJ/mol | C | Sabbah and Rojas Aguilar, 1995 | HCl(1:600 H2O), see Sabbah and Rojas Aguilar, 1995, 2; ALS |
ΔsubH° | 107.9 | kJ/mol | C | Adedeji, Lalage, et al., 1975 | AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
103.3 ± 0.5 | 344. | ME | Ribeiro da Silva, Fonseca, et al., 2005 | Based on data from 333. to 356. K.; AC |
101.9 | 413. | C | Adedeji, Lalage, et al., 1975 | AC |
88. ± 2. | 333. | V | Wolf and Weghofer, 1938 | ALS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
34.260 | 513.53 | N/A | Sabbath and Hirtz, 1991 | DH |
30.91 | 512.5 | DSC | Ribeiro da Silva, Fonseca, et al., 2005 | AC |
13.5 | 512.3 | AC | Tan, Sun, et al., 2002 | This value is considerably lower than the other three reported enthalpies of fusion. This value is likely in error.; AC |
32.26 | 512.9 | N/A | Acree, 1991 | AC |
34.26 | 513.5 | N/A | Sabbah and Hirtz, 1991 | AC |
32.260 | 512.9 | N/A | Andrews, Lynn, et al., 1926, 2 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
62.9 | 512.9 | Andrews, Lynn, et al., 1926, 2 | DH |
References
Go To: Top, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Kaluszyner and Reuter, 1953
Kaluszyner, A.; Reuter, S.,
The Reaction of Ethyl Trichloroacette with Aromatic Grignard Compounds,
J. Am. Chem. Soc., 1953, 75, 5126. [all data]
Cope and Schmitz, 1950
Cope, A.C.; Schmitz, W.R.,
Cyclic Polyolefins VII. Structure of the Eight-membered Cyclic Dimer of Chloroprene,
J. Am. Chem. Soc., 1950, 72, 3056. [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]
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]
Sabbah and Rojas Aguilar, 1995, 2
Sabbah, R.; Rojas Aguilar, A.,
Combustion calorimetry on samples of mass about 5 mg of substances containing chlorine with a CRMT rocking-bomb calorimeter. Application to the study of p-chlorobenzoic acid,
J. Chem. Thermodyn., 1995, 27, 685-691. [all data]
Adedeji, Lalage, et al., 1975
Adedeji, Festus A.; Lalage, D.; Brown, S.; Connor, Joseph A.; Leung, May L.; Paz-Andrade, I. Maria; Skinner, Henry A.,
Thermochemistry of arene chromium tricarbonyls and the strenghts of arene-chromium bonds,
Journal of Organometallic Chemistry, 1975, 97, 2, 221-228, https://doi.org/10.1016/S0022-328X(00)89468-1
. [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]
Tan, Sun, et al., 2002
Tan, Zhi-Cheng; Sun, Li-Xian; Meng, Shuang-He; Li, Li; Xu, Fen; Yu, Ping; Liu, Bei-Ping; Zhang, Ji-Biao,
Heat capacities and thermodynamic functions of p-chlorobenzoic acid,
The Journal of Chemical Thermodynamics, 2002, 34, 9, 1417-1429, https://doi.org/10.1016/S0021-9614(02)00165-9
. [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]
Notes
Go To: Top, Phase change data, References
- Symbols used in this document:
Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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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