Phenol, 3-methyl-

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Condensed phase 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δfliquid-46.19kcal/molCcbCox, 1961ALS
Δfliquid-46.38 ± 0.26kcal/molCcbAndon, Biddiscombe, et al., 1960ALS
Δfliquid-42.2kcal/molCcbPushin, 1954Author's hf298_condensed=-44.4 kcal/mol; ALS
Δfliquid-46.25kcal/molCcbBadoche, 1941Author's hf298_condensed=-48.97 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Δcliquid-885.44 ± 0.06kcal/molCcbCox, 1961Corresponding Δfliquid = -46.18 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-885.25 ± 0.14kcal/molCcbAndon, Biddiscombe, et al., 1960Corresponding Δfliquid = -46.37 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-889.4kcal/molCcbPushin, 1954Author's hf298_condensed=-44.4 kcal/mol; Corresponding Δfliquid = -42.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-885.37kcal/molCcbBadoche, 1941Author's hf298_condensed=-48.97 kcal/mol; Corresponding Δfliquid = -46.25 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-883.0kcal/molCcbBarker, 1925Author was aware that data differs from previously reported values; Corresponding Δfliquid = -48.6 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid50.810cal/mol*KN/AAndon, Counsell, et al., 1967DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
53.760298.15Andon, Counsell, et al., 1967T = 10 to 400 K.; DH
52.8093.Rastorguev and Ganiev, 1967T = 293 to 373 K.; DH
52.29298.Tschamler and Krischai, 1951DH
51.79283.Bramley, 1916Mean value, 0 to 20 C.; DH

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

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

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

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Δr348.2 ± 1.2kcal/molCIDCAngel and Ervin, 2006gas phase; B
Δr349.5 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr350.7 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr342.7 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr343.8 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

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

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

Quantity Value Units Method Reference Comment
Δr20.6 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr23.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr10.9 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
10.9423.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
Δr-4.39 ± 0.14kcal/molCmSunner, 1957liquid phase; Heat of hydrolysis; ALS

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)8.29 ± 0.02eVN/AN/AL

Proton affinity at 298K

Proton affinity (kcal/mol) Reference Comment
201. ± 2.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) (kcal/mol) Reference Comment
193. ± 2.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
8.36 ± 0.11EISelim, Fahmey, et al., 1991LL
8.29 ± 0.02SOikawa, Abe, et al., 1985LBLHLM
8.23EIRussell, Freiser, et al., 1983LBLHLM
8.52 ± 0.05EIPignataro, Foffani, et al., 1966RDSH
8.98EICrable and Kearns, 1962RDSH
8.41PEPalmer, Moyes, et al., 1979Vertical value; LLK
8.52PEKobayashi and Nagakura, 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H5+14.60 ± 0.10?EISelim, Fahmey, et al., 1990LL
C6H7+11.37?EIRussell, Freiser, et al., 1983LBLHLM
C7H7+11.28 ± 0.05OHEISelim, Fahmey, et al., 1990LL
C7H7O+11.17HEIRussell, Freiser, et al., 1983LBLHLM
C7H7O+12.3 ± 0.1HEITait, Shannon, et al., 1962RDSH

De-protonation reactions

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

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Δr348.2 ± 1.2kcal/molCIDCAngel and Ervin, 2006gas phase; B
Δr349.5 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr350.7 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr342.7 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr343.8 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

References

Go To: Top, Condensed phase thermochemistry data, 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.

Cox, 1961
Cox, J.D., The heats of combustion of phenol and the three cresols, Pure Appl. Chem., 1961, 2, 125-128. [all data]

Andon, Biddiscombe, et al., 1960
Andon, R.J.L.; Biddiscombe, D.P.; Cox, J.D.; Handley, R.; Harrop, D.; Herington, E.F.G.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols, J. Chem. Soc., 1960, 5246-5254. [all data]

Pushin, 1954
Pushin, N.A., Heats of combustion and heats of formation of isomeric organic compounds, Bull. Soc. Chim. Belgrade, 1954, 19, 531-547. [all data]

Badoche, 1941
Badoche, M., No 19. - Chaleurs de combustion du phenol, du-m-cresol et del leurs ethers; par M. Marius BADOCHE., Bull. Soc. Chim. Fr., 1941, 8, 212-220. [all data]

Barker, 1925
Barker, M.F., Calorific value and constitution, J. Phys. Chem., 1925, 29, 1345-1363. [all data]

Andon, Counsell, et al., 1967
Andon, R.J.L.; Counsell, J.F.; Lees, E.B.; Martin, J.F.; Mash, C.J., Thermodynamic properties of organic oxygen compounds. Part 17. Low-temperature heat capacity and entropy of the cresols, Trans. Faraday Soc., 1967, 63, 1115-1121. [all data]

Rastorguev and Ganiev, 1967
Rastorguev, Yu.L.; Ganiev, Yu.A., Study of the heat capacity of selected solvents, Izv. Vyssh. Uchebn. Zaved. Neft Gaz. 10, 1967, No.1, 79-82. [all data]

Tschamler and Krischai, 1951
Tschamler, H.; Krischai, H., Chinolin-m-Kresol, ein stark negatives System, Monatsh. Chem., 1951, 82, 259-270. [all data]

Bramley, 1916
Bramley, A., The study of binary mixtures. Part IV. Heats of reaction and specific heats, J. Chem. Soc. (London), 1916, 109, 496-515. [all data]

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]

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]

Oikawa, Abe, et al., 1985
Oikawa, A.; Abe, H.; Mikami, N.; Ito, M., Electronic spectra and ionization potentials of rotational isomers of severaldDisubstituted benzenes, Chem. Phys. Lett., 1985, 116, 50. [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]

Pignataro, Foffani, et al., 1966
Pignataro, S.; Foffani, A.; Innorta, G.; Distefano, G., Molecular structural effects on the ionization potentials for metasubstituted aromatic compounds and for compounds of the type X-CH2-R, Z. Physik. Chem. (Frankfurt), 1966, 49, 291. [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]


Notes

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