Phenyl radical

• Formula: C₆H₅
• Molecular weight: 77.1039
• IUPAC Standard InChI: InChI=1S/C6H5/c1-2-4-6-5-3-1/h1-5H Copy

  
• IUPAC Standard InChIKey: CIUQDSCDWFSTQR-UHFFFAOYSA-N Copy
• CAS Registry Number: 2396-01-2
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Information on this page:
  • Gas phase ion energetics data
  • Vibrational and/or electronic energy levels
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
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Gas phase ion energetics data

Go To: Top, Vibrational and/or electronic energy levels, 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

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C₆H₅⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

Vibrational and/or electronic energy levels

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

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

Data compiled by: Marilyn E. Jacox

State:   C

State:   B

State:   A

State:   ?

State:   X

Additional references: Jacox, 1994, page 388; Jacox, 1998, page 346; Jacox, 2003, page 367; McMahon, McCarthy, et al., 2003

Notes

References

Go To: Top, Gas phase ion energetics data, Vibrational and/or electronic energy levels, 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]

Gunion, Gilles, et al., 1992
Gunion, R.F.; Gilles, M.K.; Polak, M.L.; Lineberger, W.C., Ultraviolet Photoelectron Spectroscopy of the Phenide, Benzyl, and Phenoxide Anions., Int. J. Mass Spectrom. Ion Proc., 1992, 117, 601, https://doi.org/10.1016/0168-1176(92)80115-H . [all data]

Hacaloglu, Gaines, et al., 1993
Hacaloglu, J.; Gaines, A.; Suzer, S., Determination of Electron Affinity of Phenyl Radical by Dissociative Electron Attachment Technique, Org. Mass Spectrom., 1993, 28, 3, 285, https://doi.org/10.1002/oms.1210280324 . [all data]

Failes, Joyce, et al., 1976
Failes, R.L.; Joyce, J.T.; Walton, E.C., The behaviour of some dimethyl and trimethyl substituted pyridines in the magnetron, J. Phys. D: Appl. Phys., 1976, 9, 1543. [all data]

Page, 1972
Page, F.M., Experimental determination of the electron affinities of inorganic radicals, Adv. Chem. Ser., 1972, 36, 68. [all data]

Butcher, Costa, et al., 1987
Butcher, V.; Costa, M.L.; Dyke, J.M.; Ellis, A.R.; Morris, A., A study of the phenyl radical by vacuum ultraviolet photoelectron spectroscopy, Chem. Phys., 1987, 115, 261. [all data]

Sergeev, Akopyan, et al., 1972
Sergeev, Yu.L.; Akopyan, M.E.; Vilesov, F.I., Photoionization of the phenyl radical, Opt. Spectrosc., 1972, 32, 121, In original 230. [all data]

Fisher, Palmer, et al., 1964
Fisher, I.P.; Palmer, T.F.; Lossing, F.P., The vertical ionization potentials of phenyl and phenoxy radicals, J. Am. Chem. Soc., 1964, 86, 2741. [all data]

Radziszewski, 1999
Radziszewski, J.G., Electronic absorption spectrum of phenyl radical, Chem. Phys. Lett., 1999, 301, 5-6, 565, https://doi.org/10.1016/S0009-2614(99)00050-0 . [all data]

Ikeda, Nakashima, et al., 1985
Ikeda, N.; Nakashima, N.; Yoshihara, K., Observation of the ultraviolet absorption spectrum of phenyl radical in the gas phase, J. Am. Chem. Soc., 1985, 107, 11, 3381, https://doi.org/10.1021/ja00297a073 . [all data]

Porter and Ward, 1965
Porter, G.; Ward, B., The Electronic Spectra of Phenyl Radicals, Proc. Roy. Soc. (London) A287, 1965, 287, 1411, 457, https://doi.org/10.1098/rspa.1965.0190 . [all data]

Tonokura, 2002
Tonokura, K., Y.Norikane, 2002, M.Koshi, Y.Nakano, S.Nakamichi, M.Goto, S.Hashimoto, M.Kawasaki, M.P.Sulbaek Andersen, et al, J. Phys. Chem. A 106, 5908. [all data]

Freel, Park, et al., 2011
Freel, K.; Park, J.; Lin, M.C.; Heaven, M.C., Cavity ring-down spectroscopy of the phenyl radical in a pulsed discharge supersonic jet expansion, Chem. Phys. Lett., 2011, 507, 4-6, 216, https://doi.org/10.1016/j.cplett.2011.03.081 . [all data]

Pacansky and Brown, 1983
Pacansky, J.; Brown, D.W., Photolysis of acetyl benzoyl peroxide isolated in an argon matrix: the stability of the benzoyloxy and acetoxy radicals towards decarboxylation, J. Phys. Chem., 1983, 87, 9, 1553, https://doi.org/10.1021/j100232a020 . [all data]

Hatton, Hacker, et al., 1990
Hatton, W.G.; Hacker, N.P.; Kasai, P.H., J. Chem. Soc., 1990, Chem. Commun. 227. [all data]

Radziszewski, Nimlos, et al., 1996
Radziszewski, J.G.; Nimlos, M.R.; Winter, P.R.; Ellison, G.B., Infrared Absorption Spectroscopy of the Phenyl Radical, J. Am. Chem. Soc., 1996, 118, 31, 7400, https://doi.org/10.1021/ja960617+ . [all data]

Winkler and Sander, 2000
Winkler, M.; Sander, W., Isolation of the Phenyl Cation in a Solid Argon Matrix, Angew. Chem. Int. Ed., 2000, 39, 11, 2014, https://doi.org/10.1002/1521-3773(20000602)39:11<2014::AID-ANIE2014>3.0.CO;2-E . [all data]

Friderichsen, Radziszewski, et al., 2001
Friderichsen, A.V.; Radziszewski, J.G.; Nimlos, M.R.; Winter, P.R.; Dayton, D.C.; David, D.E.; Ellison, G.E., The Infrared Spectrum of the Matrix-Isolated Phenyl Radical, J. Am. Chem. Soc., 2001, 123, 9, 1977, https://doi.org/10.1021/ja0024338 . [all data]

Lapinski, Spanget-Larsen, et al., 2001
Lapinski, A.; Spanget-Larsen, J.; Langgard, M.; Waluk, J.; Radziszewski, J.G., Raman Spectrum of the Phenyl Radical, J. Phys. Chem. A, 2001, 105, 46, 10520, https://doi.org/10.1021/jp0114900 . [all data]

Pacansky and Bargon, 1975
Pacansky, J.; Bargon, J., Low temperature photochemical studies on acetyl benzoyl peroxide. Observation of methyl and phenyl radicals by matrix isolation infrared spectroscopy, J. Am. Chem. Soc., 1975, 97, 23, 6896, https://doi.org/10.1021/ja00856a066 . [all data]

Pacansky, Gardini, et al., 1976
Pacansky, J.; Gardini, G.P.; Bargon, J., Low temperature studies on propionyl benzoyl peroxide and propionyl peroxide. The ethyl radical, J. Am. Chem. Soc., 1976, 98, 9, 2665, https://doi.org/10.1021/ja00425a045 . [all data]

Miller, Andrews, et al., 1980
Miller, J.H.; Andrews, L.; Lund, P.A.; Schatz, P.N., Argon matrix photolysis and photoionization studies of benzene. Absorption spectrum of benzene cation and benzene dimer cation, J. Chem. Phys., 1980, 73, 10, 4932, https://doi.org/10.1063/1.440023 . [all data]

Jacox, 1982
Jacox, M.E., Reaction of fluorine atoms with benzene. Vibrational spectrum of the 1-fluorocyclohexadienyl radical intermediate trapped in solid argon, J. Phys. Chem., 1982, 86, 5, 670, https://doi.org/10.1021/j100394a016 . [all data]

Sharp, Roberts, et al., 2008
Sharp, E.N.; Roberts, M.A.; Nesbitt, D.J., Rotationally resolved infrared spectroscopy of a jet-cooled phenyl radical in the gas phase, Phys. Chem. Chem. Phys., 2008, 10, 44, 6592, https://doi.org/10.1039/b813256a . [all data]

Jacox, 1994
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules, American Chemical Society, Washington, DC, 1994, 464. [all data]

Jacox, 1998
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules: supplement A, J. Phys. Chem. Ref. Data, 1998, 27, 2, 115-393, https://doi.org/10.1063/1.556017 . [all data]

Jacox, 2003
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules: supplement B, J. Phys. Chem. Ref. Data, 2003, 32, 1, 1-441, https://doi.org/10.1063/1.1497629 . [all data]

McMahon, McCarthy, et al., 2003
McMahon, R.J.; McCarthy, M.C.; Gottlieb, C.A.; Dudek, J.B.; Stanton, J.F.; Thaddeus, P., The Radio Spectrum of the Phenyl Radical, Astrophys. J., 2003, 590, 1, L61, https://doi.org/10.1086/376587 . [all data]

Notes

Go To: Top, Gas phase ion energetics data, Vibrational and/or electronic energy levels, References

• Symbols used in this document:
  

  EA	Electron affinity
  ΔfH(+) ion,0K	Enthalpy of formation of positive ion at 0K

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