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Benzoyl chloride

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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-109. ± 4.2kJ/molCmCarson, Pritchard, et al., 1950Heat of formation derived by Cox and Pilcher, 1970

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
Deltafliquid-157.3 ± 0.4kJ/molCmMoselhy and Pritchard, 1975see Carson, Pritchard, et al., 1950 and Davies, Dunning, et al., 1972; ALS
Deltafliquid-160.3kJ/molCcrHu and Sinke, 1969ALS
Deltafliquid-164.4kJ/molCmCarson, Pritchard, et al., 1950Heat of hydrolysis; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3332.6kJ/molCcrHu and Sinke, 1969ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
187.0298.von Reis, 1881T = 290 to 477 K.; 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil471. ± 2.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus272.KN/ABuckingham and Donaghy, 1982BS
Tfus272.52KN/AWitschonke, 1954Uncertainty assigned by TRC = 0.35 K; TRC
Tfus272.75KN/AWitschonke, 1954Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Deltavap54.8 ± 4.2kJ/molECarson, Pritchard, et al., 1950Heat of formation derived by Cox and Pilcher, 1970; ALS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
49.6320.AStephenson and Malanowski, 1987Based on data from 305. - 470. K. See also Stull, 1947 and Dykyj, Svoboda, et al., 1999.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
305.3 - 470.44.612961978.427-41.011Stull, 1947Coefficents calculated by NIST from author's data.

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 by: 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

Water + Benzoyl chloride = Benzoic acid + Hydrogen chloride

By formula: H2O + C7H5ClO = C7H6O2 + HCl

Quantity Value Units Method Reference Comment
Deltar-34.04 ± 0.21kJ/molCmMoselhy and Pritchard, 1975liquid phase; solvent: Diphenyl-ether; see Carson, Pritchard, et al., 1950 and Davies, Dunning, et al., 1972
Deltar-101.9kJ/molCmCarson, Pritchard, et al., 1950liquid phase; Heat of hydrolysis

Benzenamine, 4-methoxy- + Benzoyl chloride = p-Benzanisidide + Hydrogen chloride

By formula: C7H9NO + C7H5ClO = C14H13NO2 + HCl

Quantity Value Units Method Reference Comment
Deltar-168. ± 0.8kJ/molCacKiselev, Khuzyasheva, et al., 1979liquid phase; solvent: Benzene

p-Aminotoluene + Benzoyl chloride = Benzamide, N-(4-methylphenyl)- + Hydrogen chloride

By formula: C7H9N + C7H5ClO = C14H13NO + HCl

Quantity Value Units Method Reference Comment
Deltar-164. ± 1.kJ/molCacKiselev, Khuzyasheva, et al., 1979liquid phase; solvent: Benzene

Aniline + Benzoyl chloride = Hydrogen chloride + Benzamide, N-phenyl-

By formula: C6H7N + C7H5ClO = HCl + C13H11NO

Quantity Value Units Method Reference Comment
Deltar-149. ± 0.8kJ/molCacKiselev, Khuzyasheva, et al., 1979liquid phase; solvent: Benzene

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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity Value Units Method Reference Comment
IE (evaluated)9.53eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
9.54PEGan, Livett, et al., 1984LBLHLM
9.52PEMeeks, Wahlborg, et al., 1981LLK
9.69PIMcLoughlin and Traeger, 1979LLK
9.92EIElder, Beynon, et al., 1976LLK
9.85EIBenoit, 1973LLK
9.70 ± 0.01EIFoffani, Pignataro, et al., 1964RDSH
9.79PEGan, Livett, et al., 1984Vertical value; LBLHLM
10.0PEMeeks, Wahlborg, et al., 1981Vertical value; LLK
9.79PEGofman, Yarzhemsky, et al., 1980Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H5+13.81Cl+COEIBenoit, 1973LLK
C6H5O+10.18ClEIElder, Beynon, et al., 1976LLK
C7H5O+9.69ClPIMcLoughlin and Traeger, 1979LLK
C7H5O+10.31ClEIBenoit, 1973LLK
C7H5O+10.5ClEIMajer and Patrick, 1963RDSH

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)

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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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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 NIST Mass Spectrometry Data Center
NIST MS number 333883

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Gas Chromatography

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), NIST Free Links, 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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedSE-30150.1080.Tiess, 1984Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-11036.5Sun and Stremple, 200330. m/0.25 mm/0.25 «mu»m, He, 3. K/min; Tstart: 40. C; Tend: 325. C
CapillaryDB-11038.Gandhe, Malhotra, et al., 198930. m/0.32 mm/0.25 «mu»m, N2, 60. C @ 2. min, 8. K/min; Tend: 200. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryVF-5MS1095.1Tret'yakov, 200730. m/0.25 mm/0.25 «mu»m, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxanes1046.Zenkevich, 2001Program: not specified

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), Gas Chromatography, NIST Free Links, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Carson, Pritchard, et al., 1950
Carson, A.S.; Pritchard, H.O.; Skinner, H.A., The heats of hydrolysis of the benzoyl halides, J. Chem. Soc., 1950, 656-659. [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]

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]

Davies, Dunning, et al., 1972
Davies, J.V.; Dunning, B.K.; Pritchard, H.O., The enthalpy of formation of benzoyl chloride, J. Chem. Thermodyn., 1972, 4, 731-737. [all data]

Hu and Sinke, 1969
Hu, A.T.; Sinke, G.C., Combustion calorimetry of some chlorinated organic compounds, J. Chem. Thermodyn., 1969, 1, 507-513. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Witschonke, 1954
Witschonke, C.R., Freezing point and purity data for some organic compounds, Anal. Chem., 1954, 26, 562-4. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R., Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [all data]

Kiselev, Khuzyasheva, et al., 1979
Kiselev, V.D.; Khuzyasheva, d.G.; Konovalov, A.I., Thermochemical study of the acylation of para-substituted anilines, J. Gen. Chem. USSR, 1979, 49, 2273-2276. [all data]

Gan, Livett, et al., 1984
Gan, T.H.; Livett, M.K.; Peel, J.B., Comparative He I and He II photoelectron spectroscopic studies of the benzoyl halides, J. Chem. Soc. Faraday Trans. 2, 1984, 80, 1281. [all data]

Meeks, Wahlborg, et al., 1981
Meeks, J.; Wahlborg, A.; McGlynn, S.P., Photoelectron spectroscopy of carbonyls: Benzoic acid and its derivatives, J. Electron Spectrosc. Relat. Phenom., 1981, 22, 43. [all data]

McLoughlin and Traeger, 1979
McLoughlin, R.G.; Traeger, J.C., A photoionization study of some benzoyl compounds - thermochemistry of [C7H5O]+ formation, Org. Mass Spectrom., 1979, 14, 434. [all data]

Elder, Beynon, et al., 1976
Elder, J.F.; Beynon, J.H.; Cooks, R.G., The benzoyl ion. Thermochemistry and kinetic energy release, Org. Mass Spectrom., 1976, 11, 415. [all data]

Benoit, 1973
Benoit, F., The benzoyl cation: The participation of isolated electronic excited states in the dissociation of molecular ions of the form [C6H5COX]+, Org. Mass Spectrom., 1973, 7, 1407. [all data]

Foffani, Pignataro, et al., 1964
Foffani, A.; Pignataro, S.; Cantone, B.; Grasso, F., Ionization potentials and substituent effects for aromatic carbonyl compounds, Z. Physik. Chem. (Frankfurt), 1964, 42, 221. [all data]

Gofman, Yarzhemsky, et al., 1980
Gofman, M.M.; Yarzhemsky, V.G.; Nefedov, V.I., Relative intensities in the He(I) and He(II) photoelectron spectra of benzoyl chloride, J. Electron Spectrosc. Relat. Phenom., 1980, 21, 171. [all data]

Majer and Patrick, 1963
Majer, J.R.; Patrick, C.R., Appearance potentials of the benzoyl radical-ion, J. Chem. Soc. Faraday Trans., 1963, 59, 1274. [all data]

Tiess, 1984
Tiess, D., Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30, Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [all data]

Sun and Stremple, 2003
Sun, G.; Stremple, P., Retention index characterization of flavor, fragrance, and many other compounds on DB-1 and DB-XLB, 2003, retrieved from http://www.chem.agilent.com/cag/cabu/pdf/b-0279.pdf. [all data]

Gandhe, Malhotra, et al., 1989
Gandhe, B.R.; Malhotra, R.C.; Gutch, P.K., Gas chromatographic retention indices of tear gases on capillary columns, J. Chromatogr., 1989, 479, 165-169, https://doi.org/10.1016/S0021-9673(01)83328-8 . [all data]

Tret'yakov, 2007
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]

Zenkevich, 2001
Zenkevich, I.G., Encyclopedia of Chromatography. Derivatization of Amines, Amino Acids, Amides and Imides for GC Analysis, Marcel Dekker, Inc, New York - Basel, 2001, 224. [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), Gas Chromatography, NIST Free Links, References