Benzoic acid, phenyl ester
- Formula: C13H10O2
- Molecular weight: 198.2173
- IUPAC Standard InChIKey: FCJSHPDYVMKCHI-UHFFFAOYSA-N
- CAS Registry Number: 93-99-2
- 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: Phenyl benzoate
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Gas phase thermochemistry data
Go To: Top, Phase change data, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -34.0 ± 0.6 | kcal/mol | Ccb | Carson, Fine, et al., 1971 | see Adams, Fine, et al., 1967 |
ΔfH°gas | -36.3 ± 1.1 | kcal/mol | Ccb | Kiparisova and Rabinovich, 1971 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -36.2 ± 1.1 kcal/mol |
ΔfH°gas | -36. | kcal/mol | Ccb | Fine and Gray, 1967 |
Phase change data
Go To: Top, Gas phase thermochemistry data, 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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 571.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 344.15 | K | N/A | Beringer, Brierley, et al., 1953 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 341. | K | N/A | Reychler, 1908 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 23.7 ± 0.1 | kcal/mol | N/A | Carson, Fine, et al., 1971, 2 | AC |
ΔsubH° | 23.7 ± 0.1 | kcal/mol | V | Carson, Fine, et al., 1971 | see Adams, Fine, et al., 1967; ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
14.9 | 394. | A | Stephenson and Malanowski, 1987 | Based on data from 379. to 587. K. See also Stull, 1947.; 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 |
---|---|---|---|---|---|
380.0 to 587. | 4.72084 | 2579.911 | -40.606 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, 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:
LL - Sharon G. Lias and Joel F. Liebman
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) | 8.8 ± 0.15 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.76 | PI | Orlov, Ponomarev, et al., 1991 | LL |
8.63 | EI | Elder, Beynon, et al., 1976 | LLK |
9.0 | EI | Turk and Shapiro, 1972 | LLK |
8.98 ± 0.05 | EI | Natalis and Franklin, 1965 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H5+ | 15.46 ± 0.05 | ? | EI | Natalis and Franklin, 1965 | RDSH |
C7H5O+ | 9.41 | OC6H5 | PI | Orlov, Ponomarev, et al., 1991 | LL |
C7H5O+ | 9.62 | OC6H5 | EI | Elder, Beynon, et al., 1976 | LLK |
C7H5O+ | 10.0 | OC6H5 | EI | Turk and Shapiro, 1972 | LLK |
C7H5O+ | 10.01 ± 0.07 | C6H50 | EI | Natalis and Franklin, 1965 | RDSH |
References
Go To: Top, Gas phase thermochemistry data, 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.
Carson, Fine, et al., 1971
Carson, A.S.; Fine, D.H.; Gray, P.; Laye, P.G.,
Standard enthalpies of formation of diphenyl oxalate and benzoic anhydride and some related bond dissociation energies,
J. Chem. Soc. B, 1971, 1611-1615. [all data]
Adams, Fine, et al., 1967
Adams, G.P.; Fine, D.H.; Gray, P.; Laye, P.G.,
Heat of formation of phenyl benzoate and related bond dissociation energies,
J. Chem. Soc. B, 1967, 720-722. [all data]
Kiparisova and Rabinovich, 1971
Kiparisova, E.G.; Rabinovich, I.B.,
Thermochemistry of a series of acyl peroxides,
Dokl. Phys. Chem. (Engl. Transl.), 1971, 199, 675-677, In original 1075. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Fine and Gray, 1967
Fine, D.H.; Gray, P.,
Explosive decomposition of solid benzoyl peroxide,
Combust. Flame, 1967, 11, 71-78. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Beringer, Brierley, et al., 1953
Beringer, F.M.; Brierley, A.; Drexler, M.; Gindler, E.M.; Lumpkin, C.C.,
Diaryliodonium Salts II. The Phenylation of Organic and Inorganic Bases,
J. Am. Chem. Soc., 1953, 75, 2708. [all data]
Reychler, 1908
Reychler, A.,
The Production and Preparation of Esters,
Chem. Centr. I, 1908, 1908, 1042. [all data]
Carson, Fine, et al., 1971, 2
Carson, A.S.; Fine, D.H.; Gray, P.; Laye, P.G.,
Standard enthalpies of formation of diphenyl oxalate and benzoic anhydride and some related bond dissociation energies,
J. Chem. Soc., B:, 1971, 1611, https://doi.org/10.1039/j29710001611
. [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]
Orlov, Ponomarev, et al., 1991
Orlov, V.M.; Ponomarev, D.A.; Misharev, A.D.; Takhistov, V.V.,
Photoionization mass spectrometry and the relative stabilities of aryloxy radicals,
J. Gen. Chem. USSR, 1991, 61, 2088. [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]
Turk and Shapiro, 1972
Turk, J.; Shapiro, R.H.,
Formation of benzoyl ions: A complicated cleavage reaction,
Org. Mass Spectrom., 1972, 6, 189. [all data]
Natalis and Franklin, 1965
Natalis, P.; Franklin, J.L.,
Ionization and dissociation of diphenyl and condensed ring aromatics by electron impact. II. Diphenylcarbonyls and ethers,
J. Phys. Chem., 1965, 69, 2943. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, 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 ΔfH°gas Enthalpy of formation of gas at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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