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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
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
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

View reactions leading to C6H6O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.49 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)817.3kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity786.3kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.508 ± 0.001PILipert and Colson, 1990LL
8.506 ± 0.001PIFuke, Yoshiuchi, et al., 1984LBLHLM
8.49PEFuke, Yoshiuchi, et al., 1984LBLHLM
8. ± 0.PIPECOFraser-Monteiro, Fraser-Monteiro, et al., 1984LBLHLM
~8.21PEKlasinc, Kovac, et al., 1983LBLHLM
8.55PEBehan, Johnstone, et al., 1976LLK
8.47 ± 0.02PEMaier and Turner, 1973LLK
9.1 ± 0.1EIHenion and Kingston, 1973LLK
8.37PEDebies and Rabalais, 1973LLK
8.50EICooks, Bertrand, et al., 1973LLK
8.69EIJohnstone, Mellon, et al., 1971LLK
8.48 ± 0.05PEEland, 1969RDSH
8.52PEDewar and Worley, 1969RDSH
8.50 ± 0.01PIWatanabe, 1957RDSH
8.52 ± 0.02PIVilesov and Terenin, 1957RDSH
8.75PEBallard, Jones, et al., 1987Vertical value; LBLHLM
8.61PEKlasinc, Kovac, et al., 1983Vertical value; LBLHLM
8.70PEKimura, Katsumata, et al., 1981Vertical value; LLK
8.56PEPalmer, Moyes, et al., 1979Vertical value; LLK
8.69PEKobayashi, 1978Vertical value; LLK
8.73PEKobayashi and Nagakura, 1974Vertical value; LLK
8.67PEDewar, Ernstbrunner, et al., 1974Vertical value; LLK
8.56PEDebies and Rabalais, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C5H5+12.96 ± 0.10CO+HDERFraser-Monteiro, Fraser-Monteiro, et al., 1984LBLHLM
C5H5+14.2 ± 0.2CO+HEITajima and Tsuchiya, 1973LLK
C5H5+14.25CO+HEIOccolowitz and White, 1968RDSH
C5H6+11.4 ± 0.1COTRPILifshitz and Malinovich, 1984LBLHLM
C5H6+12.5 ± 0.1COEIHenion and Kingston, 1973LLK
C5H6+11.67COEIHowe and Williams, 1969RDSH
C5H6+[c-C5H6]11.59 ± 0.10COPIPECOFraser-Monteiro, Fraser-Monteiro, et al., 1984T = 0K; LBLHLM

De-protonation reactions

phenoxide anion + Hydrogen cation = Phenol

By formula: C6H5O- + H+ = C6H6O

Quantity Value Units Method Reference Comment
Δr1462. ± 10.kJ/molAVGN/AAverage of 6 out of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Δr1432. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; Shiner, Vorner, et al., 1986: tautomer acidities ΔHacid(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
Δr1426. ± 7.9kJ/molCIDCAngel and Ervin, 2004gas phase; B
Δr1437. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; B
Δr>1429. ± 7.5kJ/molH-TSRichardson, Stephenson, et al., 1975gas phase; B


Go To: Top, Gas phase ion energetics data, 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, . [all data]

Lipert and Colson, 1990
Lipert, R.J.; Colson, S.D., Accurate ionization potentials of phenol and phenol-(H2O) from the electric field dependence of the pump-probe photoionization threshold, J. Chem. Phys., 1990, 92, 3240. [all data]

Fuke, Yoshiuchi, et al., 1984
Fuke, K.; Yoshiuchi, H.; Kaya, K.; Achiba, Y.; Sato, K.; Kimura, K., Multiphoton ionization photoelectron spectroscopy and two-color multiphoton ionization threshold spectroscopy on the hydrogen bonded phenol and 7-azaindole in a supersonic jet, Chem. Phys. Lett., 1984, 108, 179. [all data]

Fraser-Monteiro, Fraser-Monteiro, et al., 1984
Fraser-Monteiro, M.L.; Fraser-Monteiro, L.; de Wit, J.; Baer, T., Dissociation dynamics of energy-selected phenol ions, J. Phys. Chem., 1984, 88, 3622. [all data]

Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H., Photoelectron spectra of acenes. Electronic structure and substituent effects, Pure Appl. Chem., 1983, 55, 289. [all data]

Behan, Johnstone, et al., 1976
Behan, J.M.; Johnstone, R.A.W.; Bentley, T.W., An evaluation of empirical methods for calculating the ionization potentials of substituted benzenes, Org. Mass Spectrom., 1976, 11, 207. [all data]

Maier and Turner, 1973
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [all data]

Henion and Kingston, 1973
Henion, J.D.; Kingston, D.G.I., Mass spectrometry of organic compounds. VII. Energetics of substituent isomerization in diphenyl sulfide and diphenyl ether, J. Am. Chem. Soc., 1973, 95, 8358. [all data]

Debies and Rabalais, 1973
Debies, T.P.; Rabalais, J.W., Photoelectron spectra of substituted benzenes. II. Seven valence electron substituents, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 355. [all data]

Cooks, Bertrand, et al., 1973
Cooks, R.G.; Bertrand, M.; Beynon, J.H.; Rennekamp, M.E.; Setser, D.W., Energy partitioning data as an ion structure probe. Substituted anisoles, J. Am. Chem. Soc., 1973, 95, 1732. [all data]

Johnstone, Mellon, et al., 1971
Johnstone, R.A.W.; Mellon, F.A.; Ward, S.D., On-line computer methods used in conjunction with the measurement of ionization appearance potentials, Adv. Mass Spectrom., 1971, 5, 334. [all data]

Eland, 1969
Eland, J.H.D., Photoelectron spectra of conjugated hydrocarbons and heteromolecules, Intern. J. Mass Spectrom. Ion Phys., 1969, 2, 471. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N., The photoionization of the vapors of certain organic compounds, Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]

Ballard, Jones, et al., 1987
Ballard, R.E.; Jones, J.; Read, D.; Inchley, A.; Cranmer, M., He(I) photoelectron studies of liquids and gases, Chem. Phys. Lett., 1987, 137, 125. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Speirs, M.; Ridyard, J.N.A., The electronic structure of substituted benzenes; ab initio calculations and photoelectron spectra for phenol, the methyl- and fluoro-derivatives, and the dihydroxybenzenes, J. Mol. Struct., 1979, 52, 293. [all data]

Kobayashi, 1978
Kobayashi, T., A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes, Phys. Lett., 1978, 69, 105. [all data]

Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S., Photoelectron spectra of substituted benzenes, Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]

Dewar, Ernstbrunner, et al., 1974
Dewar, P.S.; Ernstbrunner, E.; Gilmore, J.R.; Godfrey, M.; Mellor, J.M., Conformational analysis of alkyl aryl ethers and alkyl aryl sulphides by photoelectron spectroscopy, Tetrahedron, 1974, 30, 2455. [all data]

Tajima and Tsuchiya, 1973
Tajima, S.; Tsuchiya, T., Energetics consideration of C5H5+ ions produced from various precursors by electron impact, Bull. Chem. Soc. Jpn., 1973, 46, 3291. [all data]

Occolowitz and White, 1968
Occolowitz, J.L.; White, G.L., Energetic considerations in the assignment of some fragment ion structures, Australian J. Chem., 1968, 21, 997. [all data]

Lifshitz and Malinovich, 1984
Lifshitz, C.; Malinovich, Y., Time resolved photoionization mass spectrometry in the millisecond range, Int. J. Mass Spectrom. Ion Processes, 1984, 60, 99. [all data]

Howe and Williams, 1969
Howe, I.; Williams, D.H., Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes, J. Am. Chem. Soc., 1969, 91, 7137. [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, . [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, . [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]

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]


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