Benzophenone

• Formula: C₁₃H₁₀O
• Molecular weight: 182.2179
• IUPAC Standard InChI: InChI=1S/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H Copy

  
• IUPAC Standard InChIKey: RWCCWEUUXYIKHB-UHFFFAOYSA-N Copy
• CAS Registry Number: 119-61-9
• 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: Methanone, diphenyl-; α-Oxodiphenylmethane; α-Oxoditane; Benzene, benzoyl-; Benzoylbenzene; Diphenyl ketone; Diphenylmethanone; Phenyl ketone; Ketone, diphenyl; alpha-Oxodiphenylmethane; alpha-Oxoditane; Adjutan 6016; Kayacure BP; Diphenyl-methanon; NSC 8077; 1-Benzophenone; Cinnarizine M (benzophenone); Cyclizine M (Benzophenone)
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• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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

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: José A. Martinho Simões

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

C₁₃H₁₀NaO (solution) + 0.5 (solution) = C₄CoNaO₄ (solution) +  (solution)

By formula: C₁₃H₁₀NaO (solution) + 0.5C₈Co₂O₈ (solution) = C₄CoNaO₄ (solution) + C₁₃H₁₀O (solution)

 (solution) +  (cr) = C₁₃H₁₀NaO (solution)

By formula: C₁₃H₁₀O (solution) + Na (cr) = C₁₃H₁₀NaO (solution)

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:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

View reactions leading to C₁₃H₁₀O⁺ (ion structure unspecified)

Electron affinity determinations

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% CCl4 FOR 3800-1330, 10% CS2 FOR 1330-440 CM^-1) $$ 99.99% PRINCETON ORGANICS; DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

Data compiled by: Timothy J. Johnson, Tanya L. Myers, Yin-Fong Su, Russell G. Tonkyn, Molly Rose K. Kelly-Gorham, and Tyler O. Danby

• solid; Bruker Tensor 37 FTIR; 0.96450084 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

UV/Visible spectrum

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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Sabbah and Laffitte, 1978
Sabbah, R.; Laffitte, M., Etude thermodynamique de la molecule de benzophenone, Thermochim. Acta, 1978, 23, 196-198. [all data]

Kiss, Nolan, et al., 1994
Kiss, G.; Nolan, S.P.; Hoff, C.D., Inorg. Chim. Acta, 1994, 227, 285. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Grimsrud, Caldwell, et al., 1985
Grimsrud, E.; Caldwell, G.; Kebarle, P., Electron affinities from electron transfer equilibria: A- + B = A + B-, J. Am. Chem. Soc., 1985, 107, 4627. [all data]

Maeyama, Yagi, et al., 2008
Maeyama, T.; Yagi, I.; Fujii, A.; Mikami, N., Photoelectron spectroscopy of microsolvated benzophenone radical anions to reveal the origin of solvatochromic shifts in alcoholic media, Chem. Phys. Lett., 2008, 457, 1-3, 18-22, https://doi.org/10.1016/j.cplett.2008.03.055 . [all data]

Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H., Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase, Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083 . [all data]

Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr., Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO₂) from 74CEL/BEN], J. Am. Chem. Soc., 1985, 107, 2291. [all data]

Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S., Electron affinities and electron transfer reactions, Chem. Rev., 1987, 87, 513. [all data]

Chen and Wentworth, 1983
Chen, E.C.M.; Wentworth, W.E., Determination of molecular electron affinities using the electron capture detector in the pulse sampling mode at steady state, J. Phys. Chem., 1983, 87, 45. [all data]

Grutzmacher and Schubert, 1979
Grutzmacher, H.-F.; Schubert, R., Substituent effects in the mass spectra of benzoyl hetarenes, Org. Mass Spectrom., 1979, 14, 567. [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]

Krenmayr, Heller, et al., 1974
Krenmayr, P.; Heller, R.; Varmuza, K., Massenspektrometrische untersuchungen an benzophenon und substituierten benzophenonen. I. Ermittlung thermodynamischer grossen, Org. Mass Spectrom., 1974, 9, 998. [all data]

Heller, Varmuza, et al., 1974
Heller, R.; Varmuza, K.; Krenmayr, P., Massenspektrometrische untersuchung des substituenteneffektes bei einfach substituierten benzophenonen, Monatsh. Chem., 1974, 105, 787. [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]

Iskakov and Potapov, 1971
Iskakov, L.I.; Potapov, V.K., Photionization and decomposition of benzaldehyde, acetophenone, and benzophenone, High Energy Chem., 1971, 5, 238, In original 265. [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]

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]

Terenin, 1961
Terenin, A., Charge transfer in organic solids, induced by light, Proc. Chem. Soc., London, 1961, 321. [all data]

McAlduff and Bunbury, 1979
McAlduff, E.J.; Bunbury, D.L., Photoelectron spectra of some aromatic mono-and di-ketones, J. Electron Spectrosc. Relat. Phenom., 1979, 17, 81. [all data]

Centineo, Fragala, et al., 1978
Centineo, G.; Fragala, I.; Bruno, G.; Spampinato, S., Photoelectron spectroscopy of benzophenone, acetophenone and their ortho-alkyl derivatives, J. Mol. Struct., 1978, 44, 203. [all data]

Terenin and Ermolaev, 1952
Terenin, A.N.; Ermolaev, V.L., Sensibilized phosphorescence of organic molecules at low temperatures, Dokl. Akad. Nauk SSSR, 1952, 85, 3, 547-550. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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