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Phenol, 3-methyl-

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Reaction 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.

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

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Individual Reactions

C7H7O- + Hydrogen cation = Phenol, 3-methyl-

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Deltar1457. ± 5.0kJ/molCIDCAngel and Ervin, 2006gas phase; B
Deltar1462. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1467. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar1434. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1438. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

Bromine anion + Phenol, 3-methyl- = (Bromine anion bullet Phenol, 3-methyl-)

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

Quantity Value Units Method Reference Comment
Deltar86.2 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar96.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar45.6 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

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

m-Cresyl acetate + Water = Phenol, 3-methyl- + Acetic acid

By formula: C9H10O2 + H2O = C7H8O + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-18.4 ± 0.59kJ/molCmSunner, 1957liquid phase; Heat of hydrolysis; ALS

References

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

Angel and Ervin, 2006
Angel, L.A.; Ervin, K.M., Gas-phase acidities and O-H bond dissociation enthalpies of phenol, 3-methylphenol, 2,4,6-trimethylphenol, and ethanoic acid, J. Phys. Chem. A, 2006, 110, 35, 10392-10403, https://doi.org/10.1021/jp0627426 . [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]

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]

Sunner, 1957
Sunner, S., The heat of hydrolysis of i-propenyl acetate and m-cresyl acetate and the heat of formation of acetone, Acta Chem. Scand., 1957, 11, 1757-1760. [all data]


Notes

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