Benzene, hexafluoro-

• Formula: C₆F₆
• Molecular weight: 186.0546
• IUPAC Standard InChI: InChI=1S/C6F6/c7-1-2(8)4(10)6(12)5(11)3(1)9 Copy

  
• IUPAC Standard InChIKey: ZQBFAOFFOQMSGJ-UHFFFAOYSA-N Copy
• CAS Registry Number: 392-56-3
• 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: CP 28; Hexafluorobenzene; Perfluorobenzene; 1,2,3,4,5,6-Hexafluorobenzene
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• Information on this page:
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • 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 ion energetics data

Go To: Top, 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:
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
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
B - John E. Bartmess

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

References

Go To: Top, 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.

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]

Miller, Van Doren, et al., 2004
Miller, T.M.; Van Doren, J.M.; Viggiano, A.A., Electron attachment and detachment: C6F6, Int. J. Mass Spectrom., 2004, 233, 1-3, 67-73, https://doi.org/10.1016/j.ijms.2003.11.014 . [all data]

Dillow and Kebarle, 1989
Dillow, G.W.; Kebarle, P., Substituent Effects on the Electron Affinities of Perfluorobenzenes C₆F₅X, J. Am. Chem. Soc., 1989, 111, 15, 5592, https://doi.org/10.1021/ja00197a014 . [all data]

Eustis, Wang, et al., 2007
Eustis, S.N.; Wang, D.; Bowen, K.H.; Patwari, G.N., Photoelectron spectroscopy of hydrated hexafluorobenzene anions, J. Chem. Phys., 2007, 127, 11, 114312, https://doi.org/10.1063/1.2768349 . [all data]

Christophorou and Datkos, 1995
Christophorou, L.G.; Datkos, P.G., Effect of Temperature on the Formation and Autodestruction of Parent Anions, Int. J. Mass Spectrom. Ion Proc., 1995, 149/150, 59, https://doi.org/10.1016/0168-1176(95)04229-E . [all data]

Nakajima, Taguwa, et al., 1993
Nakajima, A.; Taguwa, T.; Hoshino, K.; Sugioka, T.; Naganuma, T.; Ono, F.; Watanabe, K.; Nakao, K., Photoelectron Spectroscopy of (C6F6)n- and (Au-C6F6)- Clusters, Chem. Phys. Lett., 1993, 214, 1, 22, https://doi.org/10.1016/0009-2614(93)85449-X . [all data]

Chen, Wiley, et al., 1994
Chen, E.C.M.; Wiley, J.R.; Batten, C.F.; Wentworth, W.E., Determination of the Electron Affinities of Molecules Using Negative Ion Mass Spectrometry, J. Phys. Chem., 1994, 98, 1, 88, https://doi.org/10.1021/j100052a016 . [all data]

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

Wentworth, Limero, et al., 1987
Wentworth, W.E.; Limero, T.; Chen, E.C.M., Electron Affinities of Hexafluorobenzene and Pentafluorobenzene, J. Phys. Chem., 1987, 91, 1, 241, https://doi.org/10.1021/j100285a051 . [all data]

Lifshitz, Tiernan, et al., 1973
Lifshitz, C.; Tiernan, T.O.; Hughes, B.M., Electron affinities from endothermic negative-ion charge transfer reactions. IV. SF₆, selected fluorocarbons, and other polyatomic molecules, J. Chem. Phys., 1973, 59, 3182. [all data]

Page and Goode, 1969
Page, F.M.; Goode, G.C., Negative Ions and the Magnetron., Wiley, NY, 1969. [all data]

Maier and Thommen, 1981
Maier, J.P.; Thommen, F., Fluorescence quantum yields and lifetimes of fluorobenzene cations in selected levels of their B and C states determined by photoelectron-photoion coincidence spectroscopy, Chem. Phys., 1981, 57, 319. [all data]

Bieri, Asbrink, et al., 1981
Bieri, G.; Asbrink, L.; Von Niessen, W., 30.4 nm He(II) photoelectron spectra of organic molecules. Part IV. Fluoro-compounds (C,H,F), J. Electron Spectrosc. Relat. Phenom., 1981, 23, 281. [all data]

Bastide, Hall, et al., 1979
Bastide, J.; Hall, D.; Heilbronner, E.; Maier, J.P., He(Iα) photoelectron spectra of some higher aromatic perfluoro compounds, J. Electron Spectrosc. Relat. Phenom., 1979, 16, 205. [all data]

Sell, Mintz, et al., 1978
Sell, J.A.; Mintz, D.M.; Kupperman, A., Photoelectron angular distributions of carbon-carbon π electrons in ethylene, benzene, and their fluorinated derivatives, Chem. Phys. Lett., 1978, 58, 601. [all data]

Praet, Hubin-Franskin, et al., 1977
Praet, M-Th.; Hubin-Franskin, M.J.; Delwiche, J.P.; Schoos, R., Ionization and dissociation of C₆F₆ isomers under electron impact, Org. Mass Spectrom., 1977, 12, 297. [all data]

Brundle, Robin, et al., 1972
Brundle, C.R.; Robin, M.B.; Kuebler, N.A., Perfluoro effect in photoelectron spectroscopy. II. Aromatic molecules, J. Am. Chem. Soc., 1972, 94, 1466. [all data]

Smith and Raymonda, 1971
Smith, D.R.; Raymonda, J.W., Rydberg states in fluorinated benzenes; hexa-, penta-, and mono- fluorobenzene, Chem. Phys. Lett., 1971, 12, 269. [all data]

Clark and Frost, 1967
Clark, I.D.; Frost, D.C., A study of the energy levels in benzene and some fluorobenzenes by photoelectron spectroscopy, J. Am. Chem. Soc., 1967, 89, 244. [all data]

Bralsford, Harris, et al., 1960
Bralsford, R.; Harris, P.V.; Price, W.C., The effect of fluorine on the electronic spectra and ionization potentials of molecules, Proc. Roy. Soc. (London), 1960, A258, 459. [all data]

Trudell and Price, 1979
Trudell, B.C.; Price, S.J.W., The ultraviolet photoelectron spectra of C₆F₅X compounds, X=(F, Cl, Br, I, H, CH₃), Can. J. Chem., 1979, 57, 2256. [all data]

Kobayashi, 1978
Kobayashi, T., A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes, Phys. Lett., 1978, 69, 105. [all data]

Kobayashi and Nagakura, 1975
Kobayashi, T.; Nagakura, S., Angular distribution for the photoelectron spectra of benzene and hexafluorobenzene, J. Electron Spectrosc. Relat. Phenom., 1975, 7, 187. [all data]

Streets and Ceasar, 1973
Streets, D.G.; Ceasar, G.P., Inductive mesomeric effects on the π orbitals of halobenzenes, Mol. Phys., 1973, 26, 1037. [all data]

Dibeler, Reese, et al., 1957
Dibeler, V.H.; Reese, R.M.; Mohler, F.L., Ionization and dissociation of hexafluorobenzene by electron impact, J. Chem. Phys., 1957, 26, 304. [all data]

Adams, Smith, et al., 1985
Adams, N.G.; Smith, D.; Alge, E., Anomalous temperature dependence of the coefficient of electron attachment to hexafluorobenzene, Chem. Phys. Lett., 1985, 116, 460. [all data]

Price and Sapiano, 1974
Price, S.J.W.; Sapiano, H.J., C₆F₅X bond dissociation energies: determination from appearance potential measurements and correlation with thermochemical data, Can. J. Chem., 1974, 52, 4109. [all data]

Majer and Patrick, 1962
Majer, J.R.; Patrick, C.R., Electron impact on some halogenated aromatic compounds, J. Chem. Soc. Faraday Trans., 1962, 58, 17. [all data]

Notes

Go To: Top, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy

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