Benzoic acid, phenyl ester

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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
Δfgas-142. ± 3.kJ/molCcbCarson, Fine, et al., 1971see Adams, Fine, et al., 1967
Δfgas-152.0 ± 4.7kJ/molCcbKiparisova and Rabinovich, 1971Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -151. ± 4.6 kJ/mol
Δfgas-150.kJ/molCcbFine and Gray, 1967 

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
Δfsolid-241. ± 2.kJ/molCcbCarson, Fine, et al., 1971see Adams, Fine, et al., 1967
Δfsolid-241. ± 3.kJ/molCcbKiparisova and Rabinovich, 1971 
Δfsolid-238. ± 15.kJ/molCcbFine and Gray, 1967 
Quantity Value Units Method Reference Comment
Δcsolid-6304. ± 3.kJ/molCcbKiparisova and Rabinovich, 1971Corresponding Δfsolid = -241. kJ/mol (simple calculation by NIST; no Washburn corrections)
Δcsolid-6309. ± 15.kJ/molCcbFine and Gray, 1967Corresponding Δfsolid = -236. kJ/mol (simple calculation by NIST; no Washburn corrections)

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
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
Tboil571.7KN/AAldrich Chemical Company Inc., 1990BS
Quantity Value Units Method Reference Comment
Tfus344.15KN/ABeringer, Brierley, et al., 1953Uncertainty assigned by TRC = 1.5 K; TRC
Tfus341.KN/AReychler, 1908Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Δsub99.0 ± 0.4kJ/molN/ACarson, Fine, et al., 1971, 2AC
Δsub99.0 ± 0.4kJ/molVCarson, Fine, et al., 1971see Adams, Fine, et al., 1967; ALS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
62.4394.AStephenson and Malanowski, 1987Based on data from 379. to 587. 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
380.0 to 587.4.726552579.911-40.606Stull, 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:


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:
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 ± 0.15eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
8.76PIOrlov, Ponomarev, et al., 1991LL
8.63EIElder, Beynon, et al., 1976LLK
9.0EITurk and Shapiro, 1972LLK
8.98 ± 0.05EINatalis and Franklin, 1965RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H5+15.46 ± 0.05?EINatalis and Franklin, 1965RDSH
C7H5O+9.41OC6H5PIOrlov, Ponomarev, et al., 1991LL
C7H5O+9.62OC6H5EIElder, Beynon, et al., 1976LLK
C7H5O+10.0OC6H5EITurk and Shapiro, 1972LLK
C7H5O+10.01 ± 0.07C6H50EINatalis and Franklin, 1965RDSH

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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Mass 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 Japan AIST/NIMC Database- Spectrum MS-NW-4336
NIST MS number 232670

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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

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

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Column type Active phase I Reference Comment
CapillaryHP-Innowax2514.Adamiec, Rossner, et al., 200130. m/0.25 mm/0.25 μm, N2, 5. K/min; Tstart: 60. C; Tend: 220. C

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryUltra-11604.Okumura, 199125. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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, 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]

Adamiec, Rossner, et al., 2001
Adamiec, J.; Rossner, J.; Velisek, J.; Cejpek, K.; Savel, J., Minor Strecker degradation products of phenylalanine and phenylglycine, Eur. Food Res. Technol., 2001, 212, 2, 135-140, https://doi.org/10.1007/s002170000234 . [all data]

Okumura, 1991
Okumura, T., retention indices of environmental chemicals on methyl silicone capillary column, Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References