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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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 |
---|---|---|---|---|---|
ΔfH°gas | -77.6 ± 0.2 | kcal/mol | Ccr | Sabbah and Rojas Aguilar, 1995 | HCl(1:600 H2O), see Sabbah and Rojas Aguilar, 1995, 2 |
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 |
---|---|---|---|---|---|
ΔfH°solid | -102.5 ± 0.6 | kcal/mol | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -732.4 ± 0.6 | kcal/mol | AVG | N/A | Average of 13 values; Individual data points |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
40.11 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 265 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 |
---|---|---|---|---|---|
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, 2 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 25.1 ± 0.2 | kcal/mol | ME | Ribeiro da Silva, Fonseca, et al., 2005 | Based on data from 333. to 356. K.; AC |
ΔsubH° | 24.50 ± 0.1 | kcal/mol | C | Sabbah and Aguilar, 1995 | AC |
ΔsubH° | 24.50 ± 0.1 | kcal/mol | C | Sabbah and Rojas Aguilar, 1995 | HCl(1:600 H2O), see Sabbah and Rojas Aguilar, 1995, 2; ALS |
ΔsubH° | 25.79 | kcal/mol | C | Adedeji, Lalage, et al., 1975 | AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
24.7 ± 0.1 | 344. | ME | Ribeiro da Silva, Fonseca, et al., 2005 | Based on data from 333. to 356. K.; AC |
24.35 | 413. | C | Adedeji, Lalage, et al., 1975 | AC |
21.0 ± 0.4 | 333. | V | Wolf and Weghofer, 1938 | ALS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.1883 | 513.53 | N/A | Sabbath and Hirtz, 1991 | DH |
7.388 | 512.5 | DSC | Ribeiro da Silva, Fonseca, et al., 2005 | AC |
3.23 | 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 |
7.710 | 512.9 | N/A | Acree, 1991 | AC |
8.188 | 513.5 | N/A | Sabbah and Hirtz, 1991 | AC |
7.7103 | 512.9 | N/A | Andrews, Lynn, et al., 1926 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
15.0 | 512.9 | Andrews, Lynn, et al., 1926 | 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- + =
By formula: C7H4ClO2- + H+ = C7H5ClO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 335.5 ± 2.1 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 328.5 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; B |
By formula: C7H4Cl2O + H2O = C7H5ClO2 + HCl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -10.45 ± 0.10 | kcal/mol | Cm | Moselhy and Pritchard, 1975 | liquid phase; solvent: Diphenyl-ether; ALS |
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- + =
By formula: C7H4ClO2- + H+ = C7H5ClO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 335.5 ± 2.1 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 328.5 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas phase |
IR Spectrum
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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: Coblentz Society, Inc.
Spectrum
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Additional Data
View scan of original (hardcopy) spectrum.
Owner | COBLENTZ SOCIETY Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Source reference | COBLENTZ NO. 1345 |
Date | Not specified, most likely prior to 1970 |
Instrument | Not specified, most likely a prism, grating, or hybrid spectrometer. |
Data processing | (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE) |
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-1834 |
NIST MS number | 228878 |
UV/Visible spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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Source | Lang (editor), 1968 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 19074 |
Instrument | Unicam SP 700 |
Melting point | 150-152 |
Gas Chromatography
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1336. | Peng, Ding, et al., 1988 | He, Supelcoport and Chromosorb, 40. C @ 4. min, 10. K/min, 250. C @ 60. min; Column length: 3.05 m |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, NIST Subscription Links, 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]
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]
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]
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, 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]
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]
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]
Lang (editor), 1968
Lang (editor), L.,
Absorption Spectra in the Ultraviolet and Visible Region, 1968, 11, 85. [all data]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C.,
Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns,
J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8
. [all data]
Notes
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- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid 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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