Benzoic acid, phenyl ester

• Formula: C₁₃H₁₀O₂
• Molecular weight: 198.2173
• IUPAC Standard InChI: InChI=1S/C13H10O2/c14-13(11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H Copy

  
• IUPAC Standard InChIKey: FCJSHPDYVMKCHI-UHFFFAOYSA-N Copy
• 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
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• Other names: Phenyl benzoate
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• Information on this page:
  • 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
  • Notes
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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

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

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

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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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

Ionization energy determinations

Appearance energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)
• SOLUTION (10% IN CCl4 FOR 4000-1330 CM^-1, 10% IN CS2 FOR 1330-600 CM^-1); BECKMAN IR-7 (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

• gas

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

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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Normal alkane RI, non-polar column, temperature ramp

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References

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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

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• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid 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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