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:
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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
• Data at other public NIST sites:
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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:
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

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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:   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 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]

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 ion energetics data, Vibrational and/or electronic energy levels, References

• Symbols used in this document:
  

  EA	Electron affinity
  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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