p-Cresol

• Formula: C₇H₈O
• Molecular weight: 108.1378
• IUPAC Standard InChI: InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3 Copy

  
• IUPAC Standard InChIKey: IWDCLRJOBJJRNH-UHFFFAOYSA-N Copy
• CAS Registry Number: 106-44-5
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Phenol, 4-methyl-; p-Hydroxytoluene; p-Kresol; p-Methylhydroxybenzene; p-Methylphenol; p-Oxytoluene; p-Toluol; p-Tolyl alcohol; 1-Hydroxy-4-methylbenzene; 4-Cresol; 4-Hydroxytoluene; 4-Methylphenol; 1-Methyl-4-hydroxybenzene; Paracresol; Cresol, para; Paramethyl phenol; Rcra waste number U052; p-Cresylic acid; Cresol,p-; Phenol, 4-methyI; NSC 3696; 4-methylphenol ( p-cresol); p-Cresol (4-methylphenol)
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• Information on this page:
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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)

Proton affinity at 298K

Gas basicity at 298K

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₇H₇O^- +  =

By formula: C₇H₇O^- + H⁺ = C₇H₈O

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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• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  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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