Benzoyl bromide
- Formula: C7H5BrO
- Molecular weight: 185.018
- IUPAC Standard InChI: InChI=1S/C7H5BrO/c8-7(9)6-4-2-1-3-5-6/h1-5H
- IUPAC Standard InChIKey: AQIHMSVIAGNIDM-UHFFFAOYSA-N
- CAS Registry Number: 618-32-6
- Chemical structure:
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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 | -48.5 ± 6.3 | kJ/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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -107.3 ± 0.71 | kJ/mol | Cm | Carson, Pritchard, et al., 1950 | Reanalyzed by Cox and Pilcher, 1970, Original value = -106.7 kJ/mol; Heat of hydrolysis |
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
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 | 491.7 | K | N/A | Weast and Grasselli, 1989 | BS |
| Tboil | 491. to 492. | K | N/A | Buckingham and Donaghy, 1982 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 249. | K | N/A | Buckingham and Donaghy, 1982 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 58.6 ± 6.3 | kJ/mol | E | Carson, Pritchard, et al., 1950 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
Reduced pressure boiling point
| Tboil (K) | Pressure (bar) | Reference | Comment |
|---|---|---|---|
| 321. to 323. | 0.00007 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 52.3 | 335. | A | Stephenson and Malanowski, 1987 | Based on data from 320. to 492. K. See also Stull, 1947.; 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 |
|---|---|---|---|---|---|
| 320. to 491.7 | 4.85317 | 2232.563 | -31.17 | 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: C7H9NO + C7H5BrO = HBr + C14H13NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -172. ± 0.8 | kJ/mol | Cac | Kiselev, Khuzyasheva, et al., 1979 | liquid phase; solvent: Benzene |
+
=
+
By formula: C7H9N + C7H5BrO = HBr + C14H13NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -170. ± 0.8 | kJ/mol | Cac | Kiselev, Khuzyasheva, et al., 1979 | liquid phase; solvent: Benzene |
+
=
+
By formula: C7H5BrO + C6H7N = HBr + C13H11NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -162. ± 0.8 | kJ/mol | Cac | Kiselev, Khuzyasheva, et al., 1979 | liquid phase; solvent: Benzene |
+
=
+
By formula: C7H5BrO + H2O = HBr + C7H6O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -113.1 | kJ/mol | Cm | Carson, Pritchard, et al., 1950 | liquid phase; Heat of hydrolysis |
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 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
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.2 | PE | Gan, Livett, et al., 1984 | LBLHLM |
| 9.65 | PI | McLoughlin and Traeger, 1979 | LLK |
| 9.80 | PE | Gan, Livett, et al., 1984 | Vertical value; LBLHLM |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C7H5O+ | 9.65 | Br | PI | McLoughlin and Traeger, 1979 | LLK |
| C7H5O+ | 10.0 | Br | EI | Elder, Beynon, et al., 1976 | LLK |
| C7H5O+ | 10.0 | Br | EI | Majer and Patrick, 1963 | RDSH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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.
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]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]
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]
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]
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]
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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point 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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