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 thermochemistry data
  • Gas phase ion energetics data
  • Vibrational and/or electronic energy levels
  • 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.

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

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

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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: 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 thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, NIST Free Links, Notes

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

Tsang, 1996
Tsang, W., Heats of Formation of Organic Free Radicals by Kinetic Methods in Energetics of Organic Free Radicals, Martinho Simoes, J.A.; Greenberg, A.; Liebman, J.F., eds., Blackie Academic and Professional, London, 1996, 22-58. [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]

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 thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, NIST Free Links, References

• Symbols used in this document:
  

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

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