Benzoic acid, 3-chloro-
- Formula: C7H5ClO2
- Molecular weight: 156.566
- IUPAC Standard InChIKey: LULAYUGMBFYYEX-UHFFFAOYSA-N
- CAS Registry Number: 535-80-8
- 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, m-chloro-; m-Chlorobenzoic acid; 3-Chlorobenzoic acid; Acido m-clorobenzoico
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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 | -76.9 ± 0.2 | kcal/mol | Ccr | Sabbah and Rojas Aguilar, 1995 | HCl(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 |
---|---|---|---|---|---|
ΔfH°solid | -101.1 ± 0.2 | kcal/mol | Ccr | Sabbah and Rojas Aguilar, 1995 | HCl(1:600 H2O); ALS |
ΔfH°solid | -101.48 ± 0.37 | kcal/mol | Ccr | Johnson and Prosen, 1974 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -719.32 ± 0.14 | kcal/mol | Ccr | Sabbah and Rojas Aguilar, 1995 | HCl(1:600 H2O); ALS |
ΔcH°solid | -733.28 ± 0.37 | kcal/mol | Ccr | Johnson and Prosen, 1974 | ALS |
ΔcH°solid | -733.6 ± 2.0 | kcal/mol | Ccb | Smith, Bjellerup, et al., 1953 | Reanalyzed by Cox and Pilcher, 1970, Original value = -733. ± 1. kcal/mol; ALS |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
39.10 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 205 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 | 427.4 | K | N/A | Andrews, Lynn, et al., 1926, 2 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 24.5 ± 0.1 | kcal/mol | ME | Ribeiro da Silva and Santos, 2004 | Based on data from 320. to 340. K.; AC |
ΔsubH° | 24.24 ± 0.1 | kcal/mol | C | Sabbah and Aguilar, 1995 | AC |
ΔsubH° | 24.24 ± 0.1 | kcal/mol | C | Sabbah and Rojas Aguilar, 1995 | HCl(1:600 H2O); ALS |
ΔsubH° | 25.29 | kcal/mol | C | Adedeji, Lalage, et al., 1975 | AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
24.19 ± 0.1 | 330. | ME | Ribeiro da Silva, Fonseca, et al., 2005 | Based on data from 320. to 340. K.; AC |
23.8 | 413. | C | Adedeji, Lalage, et al., 1975 | AC |
19.3 ± 0.4 | 328. | V | Wolf and Weghofer, 1938 | ALS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
5.2581 | 427.83 | N/A | Sabbath and Hirtz, 1991 | DH |
5.657 | 427.9 | DSC | Ribeiro da Silva, Fonseca, et al., 2005 | AC |
5.700 | 427.4 | N/A | Acree, 1991 | AC |
5.26 | 427.8 | N/A | Sabbah and Hirtz, 1991 | AC |
5.7003 | 427.4 | N/A | Andrews, Lynn, et al., 1926 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.3 | 427.4 | 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° | 335.2 ± 2.1 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 328.2 ± 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° | -9.83 ± 0.08 | kcal/mol | Cm | Moselhy and Pritchard, 1975 | liquid phase; solvent: Diphenyl-ether; ALS |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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-1837 |
NIST MS number | 228874 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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]
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 and Santos, 2004
Ribeiro da Silva, Manuel A.V.; Santos, Luis M.N.B.F.,
Standard molar enthalpy of formation of monothiodibenzoylmethane by rotating-bomb calorimetry,
The Journal of Chemical Thermodynamics, 2004, 36, 6, 447-451, https://doi.org/10.1016/j.jct.2004.02.007
. [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]
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]
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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References
- 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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