Phenol, 2-methyl-

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Reaction thermochemistry data

Go To: Top, Gas phase ion energetics data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

Bromine anion + Phenol, 2-methyl- = (Bromine anion • Phenol, 2-methyl-)

By formula: Br- + C7H8O = (Br- • C7H8O)

Quantity Value Units Method Reference Comment
Δr86.2 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr96.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr45.6 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
45.6423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

C7H7O- + Hydrogen cation = Phenol, 2-methyl-

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Δr1462. ± 9.2kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1465. ± 12.kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr1431. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1434. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

Phenol, 4,6-di(1,1-dimethylethyl)-2-methyl- + Phenol, 2-methyl- = Phenol, 2-(1,1-dimethylethyl)-6-methyl- + Phenol, 4-(1,1-dimethylethyl)-2-methyl-

By formula: C15H24O + C7H8O = C11H16O + C11H16O

Quantity Value Units Method Reference Comment
Δr2.5 ± 3.5kJ/molEqkNesterova, Verevkin, et al., 1985liquid phase; ALS

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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

Proton affinity (kJ/mol) Reference Comment
832. ± 8.van Beelen, Koblenz, et al., 2004T = 298K; PA derived by authors from GB with protonation entropy equated to Rlnσ(B)/σ(BH+); MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
800. ± 8.van Beelen, Koblenz, et al., 2004T = 298K; PA derived by authors from GB with protonation entropy equated to Rlnσ(B)/σ(BH+); MM

Ionization energy determinations

IE (eV) Method Reference Comment
8.14EIRussell, Freiser, et al., 1983LBLHLM
8.24 ± 0.02PEMaier and Turner, 1973LLK
8.93EICrable and Kearns, 1962RDSH
8.46 ± 0.06EISelim, Fahmey, et al., 1991Vertical value; LL
8.50PEPalmer, Moyes, et al., 1979Vertical value; LLK
8.48PEKobayashi and Nagakura, 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H5+14.86 ± 0.09?EISelim, Fahmey, et al., 1990LL
C6H7+11.33CHOEIRussell, Freiser, et al., 1983LBLHLM
C7H7+11.26 ± 0.10OHEISelim, Fahmey, et al., 1990LL
C7H7O+11.20HEIRussell, Freiser, et al., 1983LBLHLM

De-protonation reactions

C7H7O- + Hydrogen cation = Phenol, 2-methyl-

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Δr1462. ± 9.2kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1465. ± 12.kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr1431. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1434. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

References

Go To: Top, Reaction thermochemistry data, 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.

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Stabilities in the Gas Phase of the Hydrogen Bonded Complexes, YC6H4OH-X-, of Substituted Phenols, YC6H4OH, with the Halide Anions X-(Cl-, Br-), Can. J. Chem., 1990, 68, 11, 2070, https://doi.org/10.1139/v90-316 . [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]

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]

Nesterova, Verevkin, et al., 1985
Nesterova, T.N.; Verevkin, S.P.; Malova, T.N.; Pilshchikov, V.A., Study of an equilibrium of tert-alkylphenols (thermodynamic analysis of the alkylation of phenols by branched olefins), Zh. Prikl. Khim. (Leningrad), 1985, 58, 827-833. [all data]

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]

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]

Maier and Turner, 1973
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part 2. Phenylethylenes, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 196. [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]

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]

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]


Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References