Benzophenone
- Formula: C13H10O
- Molecular weight: 182.2179
- IUPAC Standard InChIKey: RWCCWEUUXYIKHB-UHFFFAOYSA-N
- 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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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 | 49.9 ± 3.0 | kJ/mol | Cm | Sabbah and Laffitte, 1978 |
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -157. ± 11. | kJ/mol | RSC | Kiss, Nolan, et al., 1994 | solvent: Tetrahydrofuran |
(solution) +
(cr) = C13H10NaO (solution)
By formula: C13H10O (solution) + Na (cr) = C13H10NaO (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -161.1 ± 2.5 | kJ/mol | RSC | Kiss, Nolan, et al., 1994 | solvent: Tetrahydrofuran |
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.08 ± 0.04 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 882.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 852.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.62 ± 0.10 | IMRE | Grimsrud, Caldwell, et al., 1985 | ΔGea(423 K) = -15.3 kcal/mol; ΔSea (estimated) = +2.0 eu; B |
1.110 ± 0.040 | LPES | Maeyama, Yagi, et al., 2008 | Stated EA is Vertical Detachment Energy. Threshold adiabatic EA appears to be ca. 0.6 eV - JEB; B |
0.655 ± 0.087 | IMRE | Huh, Kang, et al., 1999 | ΔG(EA) 343K; anchored to ΔG value. Including anchor ΔS, EA is ca. 0.4 kcal/mol more bound.; B |
0.694 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -16.7 kcal/mol; ΔSea = 2.0, est. from data in Kebarle and Chowdhury, 1987; B |
0.642 ± 0.052 | ECD | Chen and Wentworth, 1983 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.4 ± 0.1 | EI | Grutzmacher and Schubert, 1979 | LLK |
9.28 | EI | Elder, Beynon, et al., 1976 | LLK |
9.5 ± 0.1 | EI | Krenmayr, Heller, et al., 1974 | LLK |
9.5 ± 0.1 | EI | Heller, Varmuza, et al., 1974 | LLK |
9.46 | EI | Benoit, 1973 | LLK |
9.14 ± 0.03 | PI | Iskakov and Potapov, 1971 | LLK |
9.46 ± 0.05 | EI | Natalis and Franklin, 1965 | RDSH |
9.35 ± 0.04 | EI | Foffani, Pignataro, et al., 1964 | RDSH |
9.4 | PI | Terenin, 1961 | RDSH |
9.05 ± 0.05 | PE | McAlduff and Bunbury, 1979 | Vertical value; LLK |
9.05 | PE | Centineo, Fragala, et al., 1978 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H5+ | 15.67 | C6H5+CO | EI | Benoit, 1973 | LLK |
C6H5+ | 16.22 ± 0.07 | ? | EI | Natalis and Franklin, 1965 | RDSH |
C7H5O+ | 12.0 ± 0.1 | C6H5 | EI | Grutzmacher and Schubert, 1979 | LLK |
C7H5O+ | 11.45 | C6H5 | EI | Elder, Beynon, et al., 1976 | LLK |
C7H5O+ | 11.4 ± 0.1 | C6H5 | EI | Heller, Varmuza, et al., 1974 | LLK |
C7H5O+ | 11.72 | C6H5 | EI | Benoit, 1973 | LLK |
C7H5O+ | 12.00 ± 0.05 | C6H5 | EI | Natalis and Franklin, 1965 | RDSH |
C12H8+ | 17.48 ± 0.12 | ? | EI | Natalis and Franklin, 1965 | RDSH |
C12H9+ | 15.28 ± 0.05 | CO+H? | EI | Natalis and Franklin, 1965 | RDSH |
C12H10+ | 12.24 ± 0.13 | CO | EI | Natalis and Franklin, 1965 | RDSH |
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
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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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118652 |
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
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Source | Terenin and Ermolaev, 1952 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 653 |
Instrument | n.i.g. |
Melting point | 47.8 |
Boiling point | 305.4 |
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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