Phenoxy radical

• Formula: C₆H₅O
• Molecular weight: 93.1033
• IUPAC Standard InChI: InChI=1S/C6H5O/c7-6-4-2-1-3-5-6/h1-5H Copy

  
• IUPAC Standard InChIKey: KHUXNRRPPZOJPT-UHFFFAOYSA-N Copy
• CAS Registry Number: 2122-46-5
• 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
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry data

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

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, 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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₆H₅O⁺ (ion structure unspecified)

Electron affinity determinations

Ionization energy determinations

Anion protonation reactions

 +  =

By formula: C₆H₅O^- + H⁺ = C₆H₆O

Vibrational and/or electronic energy levels

Go To: Top, Gas phase thermochemistry data, 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:   E

State:   D

State:   C

State:   B

State:   A

State:   X

Additional references: Jacox, 1994, page 443; Jacox, 1998, page 372; Jacox, 2003, page 407

Notes

References

Go To: Top, Gas phase thermochemistry data, 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.

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]

Kim, Yacovitch, et al., 2011
Kim, J.B.; Yacovitch, T.I.; Hock, C.; Neumark, D.M., Slow photoelectron velocity-map imaging spectroscopy of the phenoxide and thiophenoxide anions, Phys. Chem. Chem. Phys., 2011, 13, 38, 17378-17383, https://doi.org/10.1039/c1cp22211b . [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]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Shiner, Vorner, et al., 1986
Shiner, C.S.; Vorner, P.E.; Kass, S.R., Gas phase acidities and heats of formation of 2,4- and 2,5- cyclohexadien-1-one, the keto tautomers of phenol, J. Am. Chem. Soc., 1986, 108, 5699. [all data]

Capponi, Gut, et al., 1999
Capponi, M.; Gut, I.G.; Hellrung, B.; Persy, G.; Wirz, J., Ketonization equilibria of phenol in aqueous solution, Can. J. Chem., 1999, 77, 5-6, 605-613, https://doi.org/10.1139/v99-048 . [all data]

Richardson, Stephenson, et al., 1975
Richardson, J.H.; Stephenson, L.M.; Brauman, J.I., Photodetachment of electrons from phenoxides and thiophenoxide, J. Am. Chem. Soc., 1975, 97, 2967. [all data]

Dewar and David, 1980
Dewar, M.J.S.; David, D.E., Ultraviolet photoelectron spectrum of the phenoxy radical, J. Am. Chem. Soc., 1980, 102, 7387. [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]

Angel and Ervin, 2004
Angel, L.A.; Ervin, K.M., Competitive threshold collision-induced dissociation: Gas-phase acidity and O-H bond dissociation enthalpy of phenol, J. Phys. Chem. A, 2004, 108, 40, 8346-8352, https://doi.org/10.1021/jp0474529 . [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Kajii, Obi, et al., 1987
Kajii, Y.; Obi, K.; Nakashima, N.; Yoshihara, K., ArF laser flash photolysis of phenol and anisole, J. Chem. Phys., 1987, 87, 9, 5059, https://doi.org/10.1063/1.453673 . [all data]

Berho and Lesclaux, 1997
Berho, F.; Lesclaux, R., The phenoxy radical: UV spectrum and kinetics of gas-phase reactions with itself and with oxygen, Chem. Phys. Lett., 1997, 279, 5-6, 289, https://doi.org/10.1016/S0009-2614(97)01038-5 . [all data]

Platz, Nielsen, et al., 1998
Platz, J.; Nielsen, O.J.; Wallington, T.J.; Ball, J.C.; Hurley, M.D.; Straccia, A.M.; Schneider, W.F.; Sehested, J., Atmospheric Chemistry of the Phenoxy Radical, C, J. Phys. Chem. A, 1998, 102, 41, 7964, https://doi.org/10.1021/jp982221l . [all data]

Radziszewski, Gil, et al., 2001
Radziszewski, J.G.; Gil, M.; Gorski, A.; Spanget-Larsen, J.; Waluk, J.; Mroz, B.J., Electronic states of the phenoxyl radical, J. Chem. Phys., 2001, 115, 21, 9733, https://doi.org/10.1063/1.1415465 . [all data]

Porter and Wright, 1955
Porter, G.; Wright, F.J., Primary photochemical processes in aromatic molecules. Part 3. Absorption spectra of benzyl, anilino, phenoxy and related free radicals, Trans. Faraday Soc., 1955, 51, 1469, https://doi.org/10.1039/tf9555101469 . [all data]

Porter and Ward, 1964
Porter, G.; Ward, B., J. Chim. Phys., 1964, 61, 1517. [all data]

Tonokura, Ogura, et al., 2004
Tonokura, K.; Ogura, T.; Koshi, M., Near-UV Absorption Spectrum of the Phenoxyl Radical and Kinetics of Its Reaction with CH, J. Phys. Chem. A, 2004, 108, 39, 7801, https://doi.org/10.1021/jp049664b . [all data]

Pullin and Andrews, 1982
Pullin, D.; Andrews, L., The absorption spectra of the phenoxyl radical in solid argon, J. Mol. Struct., 1982, 95, 181, https://doi.org/10.1016/0022-2860(82)90143-0 . [all data]

Kesper, Diehl, et al., 1991
Kesper, K.; Diehl, F.; Simon, J.G.G.; Specht, H.; Schweig, A., Resonant two-photon ionization of phenol in methylene chloride doped solid argon using 248 nm KrF laser and 254 nm Hg lamp radiation, a comparative study. The UV/VIS absorption spectrum of phenol radical cation, Chem. Phys., 1991, 153, 3, 511, https://doi.org/10.1016/0301-0104(91)80064-O . [all data]

Spanget-Larsen, Gil, et al., 2001
Spanget-Larsen, J.; Gil, M.; Gorski, A.; Blake, D.M.; Waluk, J.; Radziszewski, J.G., Vibrations of the Phenoxyl Radical, J. Am. Chem. Soc., 2001, 123, 45, 11253, https://doi.org/10.1021/ja0113596 . [all data]

Ward, 1968
Ward, B., Spectrochim. Acta, 1968, 24A, 813. [all data]

Cheng, Witek, et al., 2008
Cheng, C.-W.; Witek, H.; Lee, Y.-P., Rovibronic bands of the A [sup 2]B[sub 2]←X [sup 2]B[sub 1] transition of C[sub 6]H[sub 5]O and C[sub 6]D[sub 5]O detected with cavity ringdown absorption near 1.2 μm, J. Chem. Phys., 2008, 129, 15, 154307, https://doi.org/10.1063/1.2992077 . [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]

Notes

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

• Symbols used in this document:
  

  EA	Electron affinity
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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