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Benzoic acid, 4-chloro-

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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
Deltafgas-324.8 ± 0.8kJ/molCcrSabbah and Rojas Aguilar, 1995HCl(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
Deltafsolid-429. ± 2.kJ/molAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Deltacsolid-3064. ± 3.kJ/molAVGN/AAverage of 13 values; Individual data points

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
167.8298.Andrews, Lynn, et al., 1926T = 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
Tfus511.KN/AKaluszyner and Reuter, 1953Uncertainty assigned by TRC = 3. K; TRC
Tfus512.KN/ACope and Schmitz, 1950Uncertainty assigned by TRC = 3. K; TRC
Tfus512.9KN/ACope and Schmitz, 1950Uncertainty assigned by TRC = 4. K; TRC
Tfus512.85KN/AAndrews, Lynn, et al., 1926, 2Uncertainty assigned by TRC = 0.4 K; TRC
Quantity Value Units Method Reference Comment
Deltasub105.2 ± 0.7kJ/molMERibeiro da Silva, Fonseca, et al., 2005Based on data from 333. - 356. K.; AC
Deltasub102.5 ± 0.4kJ/molCSabbah and Aguilar, 1995AC
Deltasub102.5 ± 0.4kJ/molCSabbah and Rojas Aguilar, 1995HCl(1:600 H2O), see Sabbah and Rojas Aguilar, 1995, 2; ALS
Deltasub107.9kJ/molCAdedeji, Lalage, et al., 1975AC

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
103.3 ± 0.5344.MERibeiro da Silva, Fonseca, et al., 2005Based on data from 333. - 356. K.; AC
101.9413.CAdedeji, Lalage, et al., 1975AC
88. ± 2.333.VWolf and Weghofer, 1938ALS

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
34.260513.53N/ASabbath and Hirtz, 1991DH
30.91512.5DSCRibeiro da Silva, Fonseca, et al., 2005AC
13.5512.3ACTan, Sun, et al., 2002This value is considerably lower than the other three reported enthalpies of fusion. This value is likely in error.; AC
32.26512.9N/AAcree, 1991AC
34.26513.5N/ASabbah and Hirtz, 1991AC
32.260512.9N/AAndrews, Lynn, et al., 1926DH

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
62.9512.9Andrews, Lynn, et al., 1926DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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- + Hydrogen cation = Benzoic acid, 4-chloro-

By formula: C7H4ClO2- + H+ = C7H5ClO2

Quantity Value Units Method Reference Comment
Deltar1404. ± 8.8kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar1374. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

Benzoyl chloride, 4-chloro- + Water = Benzoic acid, 4-chloro- + Hydrogen chloride

By formula: C7H4Cl2O + H2O = C7H5ClO2 + HCl

Quantity Value Units Method Reference Comment
Deltar-43.74 ± 0.42kJ/molCmMoselhy and Pritchard, 1975liquid 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- + Hydrogen cation = Benzoic acid, 4-chloro-

By formula: C7H4ClO2- + H+ = C7H5ClO2

Quantity Value Units Method Reference Comment
Deltar1404. ± 8.8kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Deltar1374. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas 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

A digitized version of this spectrum is not currently available.

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)

This IR spectrum is from the Coblentz Society's evaluated infrared reference spectra collection.


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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Mass spectrum
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Additional Data

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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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

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), 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis 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

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, 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]


Notes

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, References