Benzoyl chloride
- Formula: C7H5ClO
- Molecular weight: 140.567
- IUPAC Standard InChI: InChI=1S/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H
- IUPAC Standard InChIKey: PASDCCFISLVPSO-UHFFFAOYSA-N
- CAS Registry Number: 98-88-4
- 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: Benzaldehyde, α-chloro-; Benzenecarbonyl chloride; Benzoic acid, chloride; α-Chlorobenzaldehyde; UN 1736
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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 | -26.1 ± 1.0 | kcal/mol | Cm | Carson, Pritchard, et al., 1950 | Heat 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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -37.60 ± 0.09 | kcal/mol | Cm | Moselhy and Pritchard, 1975 | see Carson, Pritchard, et al., 1950 and Davies, Dunning, et al., 1972; ALS |
| ΔfH°liquid | -38.31 | kcal/mol | Ccr | Hu and Sinke, 1969 | ALS |
| ΔfH°liquid | -39.30 | kcal/mol | Cm | Carson, Pritchard, et al., 1950 | Heat of hydrolysis; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -796.50 | kcal/mol | Ccr | Hu and Sinke, 1969 | ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 44.69 | 298. | von Reis, 1881 | T = 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 |
|---|---|---|---|---|---|
| Tboil | 471. ± 2. | K | AVG | N/A | Average of 8 values; Individual data points |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 272. | K | N/A | Buckingham and Donaghy, 1982 | BS |
| Tfus | 272.52 | K | N/A | Witschonke, 1954 | Uncertainty assigned by TRC = 0.35 K; TRC |
| Tfus | 272.75 | K | N/A | Witschonke, 1954 | Uncertainty assigned by TRC = 0.2 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 13.1 ± 1.0 | kcal/mol | E | Carson, Pritchard, et al., 1950 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 11.9 | 320. | A | Stephenson and Malanowski, 1987 | Based on data from 305. to 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 (atm)
T = temperature (K)
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| Temperature (K) | A | B | C | Reference | Comment |
|---|---|---|---|---|---|
| 305.3 to 470.4 | 4.60725 | 1978.427 | -41.011 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
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
+
=
+
By formula: H2O + C7H5ClO = C7H6O2 + HCl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -8.136 ± 0.050 | kcal/mol | Cm | Moselhy and Pritchard, 1975 | liquid phase; solvent: Diphenyl-ether; see Carson, Pritchard, et al., 1950 and Davies, Dunning, et al., 1972 |
| ΔrH° | -24.35 | kcal/mol | Cm | Carson, Pritchard, et al., 1950 | liquid phase; Heat of hydrolysis |
+
=
+
By formula: C7H9NO + C7H5ClO = C14H13NO2 + HCl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -40.2 ± 0.2 | kcal/mol | Cac | Kiselev, Khuzyasheva, et al., 1979 | liquid phase; solvent: Benzene |
+
=
+
By formula: C7H9N + C7H5ClO = C14H13NO + HCl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -39.3 ± 0.3 | kcal/mol | Cac | Kiselev, Khuzyasheva, et al., 1979 | liquid phase; solvent: Benzene |
+
=
+
By formula: C6H7N + C7H5ClO = HCl + C13H11NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -35.6 ± 0.2 | kcal/mol | Cac | Kiselev, Khuzyasheva, et al., 1979 | liquid 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) | 9.53 | eV | N/A | N/A | L |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.54 | PE | Gan, Livett, et al., 1984 | LBLHLM |
| 9.52 | PE | Meeks, Wahlborg, et al., 1981 | LLK |
| 9.69 | PI | McLoughlin and Traeger, 1979 | LLK |
| 9.92 | EI | Elder, Beynon, et al., 1976 | LLK |
| 9.85 | EI | Benoit, 1973 | LLK |
| 9.70 ± 0.01 | EI | Foffani, Pignataro, et al., 1964 | RDSH |
| 9.79 | PE | Gan, Livett, et al., 1984 | Vertical value; LBLHLM |
| 10.0 | PE | Meeks, Wahlborg, et al., 1981 | Vertical value; LLK |
| 9.79 | PE | Gofman, Yarzhemsky, et al., 1980 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C6H5+ | 13.81 | Cl+CO | EI | Benoit, 1973 | LLK |
| C6H5O+ | 10.18 | Cl | EI | Elder, Beynon, et al., 1976 | LLK |
| C7H5O+ | 9.69 | Cl | PI | McLoughlin and Traeger, 1979 | LLK |
| C7H5O+ | 10.31 | Cl | EI | Benoit, 1973 | LLK |
| C7H5O+ | 10.5 | Cl | EI | Majer and Patrick, 1963 | RDSH |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- SOLUTION (10% IN CCl4 FOR 3800-1330, 10% IN CS2 FOR 1330-450 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- SOLUTION (2% IN CCl4 FOR 3800-1330, 2% IN CS2 FOR 1330-400 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
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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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 | NIST Mass Spectrometry Data Center |
| NIST MS number | 333883 |
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
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | SE-30 | 150. | 1080. | Tiess, 1984 | Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-1 | 1036.5 | Sun and Stremple, 2003 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 40. C; Tend: 325. C |
| Capillary | DB-1 | 1038. | Gandhe, Malhotra, et al., 1989 | 30. m/0.32 mm/0.25 μm, N2, 60. C @ 2. min, 8. K/min; Tend: 200. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | VF-5MS | 1095.1 | Tret'yakov, 2007 | 30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Polydimethyl siloxanes | 1046. | Zenkevich, 2001 | Program: 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, 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, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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