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p-Cresol

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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:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
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 C7H8O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.34 ± 0.03eVN/AN/AL

Proton affinity at 298K

Proton affinity (kcal/mol) Reference Comment
195. ± 2.van Beelen, Koblenz, et al., 2004T = 298K; PA derived by authors from GB with protonation entropy equated to Rln«sigma»(B)/«sigma»(BH+); MM

Gas basicity at 298K

Gas basicity (review) (kcal/mol) Reference Comment
187. ± 2.van Beelen, Koblenz, et al., 2004T = 298K; PA derived by authors from GB with protonation entropy equated to Rln«sigma»(B)/«sigma»(BH+); MM

Ionization energy determinations

IE (eV) Method Reference Comment
8.31 ± 0.08EISelim, Fahmey, et al., 1991LL
8.13EIRussell, Freiser, et al., 1983LBLHLM
8.34EIJohnstone and Mellon, 1973LLK
8.97EICrable and Kearns, 1962RDSH
8.35PEPalmer, Moyes, et al., 1979Vertical value; LLK
8.38PEKobayashi and Nagakura, 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H5+15.69 ± 0.08?EISelim, Fahmey, et al., 1990LL
C6H7+11.50?EIRussell, Freiser, et al., 1983LBLHLM
C7H7+11.67 ± 0.08OHEISelim, Fahmey, et al., 1990LL
C7H7O+11.13HEIRussell, Freiser, et al., 1983LBLHLM
C7H7O+12.4 ± 0.1HEITait, Shannon, et al., 1962RDSH

De-protonation reactions

C7H7O- + Hydrogen cation = p-Cresol

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Deltar350.2 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar350.2 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar351.6 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar343.4 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar343.4 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar344.7 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

References

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.

van Beelen, Koblenz, et al., 2004
van Beelen, E.S.E.; Koblenz, T.A.; Ingemann, S.; Hammerum, S., Experimental and theoretical evaluation of proton affinities of furan, the methylphenols, and the related anisoles, J. Phys. Chem. A, 2004, 108, 2787. [all data]

Selim, Fahmey, et al., 1991
Selim, E.T.M.; Fahmey, M.A.; Ghonime, H.S., Mass spectrometric study of molecular ions of methyl-phenol isomers using electron impact technique, Indian J. Phys., 1991, 65, 171. [all data]

Russell, Freiser, et al., 1983
Russell, D.H.; Freiser, B.S.; McBay, E.H.; Canada, D.C., The structure of decomposing [C7H7O]+ ions: Benzyl versus tropylium ion structures, Org. Mass Spectrom., 1983, 18, 474. [all data]

Johnstone and Mellon, 1973
Johnstone, R.A.W.; Mellon, F.A., Effects of induction and resonance in the calculation of ionization potentials of substituted benzenes by perturbation molecular orbital theory, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 36. [all data]

Crable and Kearns, 1962
Crable, G.F.; Kearns, G.L., Effect of substituent groups on the ionization potentials of benzenes, J. Phys. Chem., 1962, 66, 436. [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 and Nagakura, 1974
Kobayashi, T.; Nagakura, S., Photoelectron spectra of substituted benzenes, Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]

Selim, Fahmey, et al., 1990
Selim, E.T.M.; Fahmey, M.A.; Ghonime, H.S., [C7H7]+ and [C6H5]+ fragment ions produced from methylphenol isomers by electron impact, Org. Mass Spectrom., 1990, 26, 55. [all data]

Tait, Shannon, et al., 1962
Tait, J.M.S.; Shannon, T.W.; Harrison, A.G., The structure of substituted C7 ions from benzyl derivatives at the appearance potential threshold, J. Am. Chem. Soc., 1962, 84, 4. [all data]

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [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]

Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B., Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria, J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032 . [all data]


Notes

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