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Phenoxy radical


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.

Quantity Value Units Method Reference Comment
Deltafgas54. ± 6.kJ/molN/ATsang, 1996 

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)

Quantity Value Units Method Reference Comment
Proton affinity (review)857.7kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity827.kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
2.25380 ± 0.00080N/AKim, Yacovitch, et al., 2011B
2.2530 ± 0.0060LPESGunion, Gilles, et al., 1992Derived BDE from D-EA cycle: 87.6±2.2 kcal/mol; B
2.324 ± 0.099D-EABartmess, Scott, et al., 1979 Shiner, Vorner, et al., 1986: tautomer acidities «DELTA»Hacid(ortho) = 343.9±3.1 kcal, para = 340.1±2 kcal. However, Capponi, Gut, et al., 1999 based on aq. soln. results, imply 18 and 14 kcal/mol difference.; value altered from reference due to change in acidity scale; B
<2.359 ± 0.061PDRichardson, Stephenson, et al., 1975B

Ionization energy determinations

IE (eV) Method Reference Comment
8.56 ± 0.02PEDewar and David, 1980LLK
8.84EIFisher, Palmer, et al., 1964RDSH

Anion protonation reactions

phenoxide anion + Hydrogen cation = Phenol

By formula: C6H5O- + H+ = C6H6O

Quantity Value Units Method Reference Comment
Deltar1462. ± 10.kJ/molAVGN/AAverage of 6 out of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Deltar1432. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; Shiner, Vorner, et al., 1986: tautomer acidities «DELTA»Hacid(ortho) = 343.9±3.1 kcal, para = 340.1±2 kcal. However, Capponi, Gut, et al., 1999 based on aq. soln. results, imply 18 and 14 kcal/mol difference.; value altered from reference due to change in acidity scale; B
Deltar1426. ± 7.9kJ/molCIDCAngel and Ervin, 2004gas phase; B
Deltar1437. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B
Deltar>1429. ± 7.5kJ/molH-TSRichardson, Stephenson, et al., 1975gas phase; B

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


 Energy 
 (cm-1
 Med.   Transition   «lambda»min 
 (nm) 
 «lambda»max 
 (nm) 
 References

Tx = 43100 gas E-X Kajii, Obi, et al., 1987
Berho and Lesclaux, 1997
Platz, Nielsen, et al., 1998
To = 41800 Ar E-X Radziszewski, Gil, et al., 2001

State:   D


 Energy 
 (cm-1
 Med.   Transition   «lambda»min 
 (nm) 
 «lambda»max 
 (nm) 
 References

Tx gas D-X 270 300 Kajii, Obi, et al., 1987
Berho and Lesclaux, 1997
Platz, Nielsen, et al., 1998
To = 33900 Ar D-X Radziszewski, Gil, et al., 2001

State:   C


 Energy 
 (cm-1
 Med.   Transition   «lambda»min 
 (nm) 
 «lambda»max 
 (nm) 
 References

To = 25320 gas C-X 375 410 Porter and Wright, 1955
Porter and Ward, 1964
Tonokura, Ogura, et al., 2004
To = 25175 ± 10 Ar C-X 351 397 Pullin and Andrews, 1982
Kesper, Diehl, et al., 1991
Spanget-Larsen, Gil, et al., 2001
Radziszewski, Gil, et al., 2001


Vib. 
sym. 
 No.   Approximate 
 type of mode 
 cm-1   Med.   Method   References

1462 ± 20 Ar AB Pullin and Andrews, 1982
1140 ± 20 Ar AB Pullin and Andrews, 1982
920 ± 20 Ar AB Pullin and Andrews, 1982

State:   B


 Energy 
 (cm-1
 Med.   Transition   «lambda»min 
 (nm) 
 «lambda»max 
 (nm) 
 References

To = 16360 gas B-X 559 612 Porter and Ward, 1964
Ward, 1968
To = 15930 ± 10 Ar B-X 573 629 Pullin and Andrews, 1982
Kesper, Diehl, et al., 1991
Spanget-Larsen, Gil, et al., 2001
Radziszewski, Gil, et al., 2001


Vib. 
sym. 
 No.   Approximate 
 type of mode 
 cm-1   Med.   Method   References

500 T gas AB Ward, 1968
504 ± 10 Ar AB Pullin and Andrews, 1982

State:   A


 Energy 
 (cm-1
 Med.   Transition   «lambda»min 
 (nm) 
 «lambda»max 
 (nm) 
 References

To = 7681 gas A-X 1140 1310 Cheng, Witek, et al., 2008
To = 8900 T Ar A-X Radziszewski, Gil, et al., 2001


Vib. 
sym. 
 No.   Approximate 
 type of mode 
 cm-1   Med.   Method   References

a2 12 947 ± 2 gas CR Cheng, Witek, et al., 2008
13 793 ± 6 gas CR Cheng, Witek, et al., 2008
14 417 ± 2 gas CR Cheng, Witek, et al., 2008
b1 15 964 ± 5 gas CR Cheng, Witek, et al., 2008
16 866 ± 3 gas CR Cheng, Witek, et al., 2008
17 723 ± 2 gas CR Cheng, Witek, et al., 2008
18 680 ± 2 gas CR Cheng, Witek, et al., 2008
19 499 ± 5 gas CR Cheng, Witek, et al., 2008

State:   X


Vib. 
sym. 
 No.   Approximate 
 type of mode 
 cm-1   Med.   Method   References

a1 1 CH stretch 3090 w Ar IR Spanget-Larsen, Gil, et al., 2001
2 CH stretch 3065 w Ar IR Spanget-Larsen, Gil, et al., 2001
3 CH stretch 3018 w Ar IR Spanget-Larsen, Gil, et al., 2001
4 CC stretch 1550 m s Ar IR Spanget-Larsen, Gil, et al., 2001
5 CO stretch 1490 ± 25 T gas PE Gunion, Gilles, et al., 1992
5 CO stretch 1481 m Ar IR Spanget-Larsen, Gil, et al., 2001
6 Mixed 1397 w Ar IR Spanget-Larsen, Gil, et al., 2001
7 CH bend 1167 w Ar IR Spanget-Larsen, Gil, et al., 2001
8 Mixed 1038 w Ar IR Spanget-Larsen, Gil, et al., 2001
9 CCC bend 977 w Ar IR Spanget-Larsen, Gil, et al., 2001
10 Mixed 813 w Ar IR Spanget-Larsen, Gil, et al., 2001
11 CCC bend 515 ± 15 gas PE Gunion, Gilles, et al., 1992
11 CCC bend 520 w Ar IR Spanget-Larsen, Gil, et al., 2001
b1 15 HCCH torsion 1016 w Ar IR Spanget-Larsen, Gil, et al., 2001
16 Mixed 898 w m Ar IR Spanget-Larsen, Gil, et al., 2001
17 Mixed 784 s Ar IR Spanget-Larsen, Gil, et al., 2001
18 Mixed 635 vs Ar IR Spanget-Larsen, Gil, et al., 2001
19 Mixed 472 w Ar IR Spanget-Larsen, Gil, et al., 2001
b2 21 CH stretch 3074 w m Ar IR Spanget-Larsen, Gil, et al., 2001
22 CH stretch 3054 w Ar IR Spanget-Larsen, Gil, et al., 2001
23 Mixed 1515 m Ar IR Spanget-Larsen, Gil, et al., 2001
24 Mixed 1441 w Ar IR Spanget-Larsen, Gil, et al., 2001
25 Mixed 1318 w m Ar IR Spanget-Larsen, Gil, et al., 2001
26 Mixed 1266 w m Ar IR Spanget-Larsen, Gil, et al., 2001
27 Mixed 1140 w Ar IR Spanget-Larsen, Gil, et al., 2001
28 Mixed 1072 m Ar IR Spanget-Larsen, Gil, et al., 2001
29 CCC bend 616 w Ar IR Spanget-Larsen, Gil, et al., 2001
30 CO bend 446 w m Ar IR Spanget-Larsen, Gil, et al., 2001

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

Notes

wWeak
mMedium
sStrong
vsVery strong
TTentative assignment or approximate value
oEnergy separation between the v = 0 levels of the excited and electronic ground states.
xEnergy separation between the band maximum of the excited electronic state and the v = 0 level of the ground state.

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 «mu»m, 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