Benzoyl chloride
- Formula: C7H5ClO
- Molecular weight: 140.567
- 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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Phase change data
Go To: Top, Gas phase ion energetics data, References, Notes
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. |
Gas phase ion energetics data
Go To: Top, Phase change data, References, Notes
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 |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
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]
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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point 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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