Phenol, 3-methyl-
- Formula: C7H8O
- Molecular weight: 108.1378
- IUPAC Standard InChI: InChI=1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3
- IUPAC Standard InChIKey: RLSSMJSEOOYNOY-UHFFFAOYSA-N
- CAS Registry Number: 108-39-4
- 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: m-Cresol; m-Cresole; m-Cresylic acid; m-Hydroxytoluene; m-Kresol; m-Methylphenol; m-Oxytoluene; m-Toluol; 1-Hydroxy-3-methylbenzene; 3-Cresol; 3-Hydroxytoluene; 3-Methylphenol; meta-Cresol; Cresol, meta; Rcra waste number U052; Cresol,m-; NSC 8768
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Condensed phase thermochemistry data
Go To: Top, Reaction thermochemistry data, 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:
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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -46.19 | kcal/mol | Ccb | Cox, 1961 | ALS |
| ΔfH°liquid | -46.38 ± 0.26 | kcal/mol | Ccb | Andon, Biddiscombe, et al., 1960 | ALS |
| ΔfH°liquid | -42.2 | kcal/mol | Ccb | Pushin, 1954 | Author's hf298_condensed=-44.4 kcal/mol; ALS |
| ΔfH°liquid | -46.25 | kcal/mol | Ccb | Badoche, 1941 | Author's hf298_condensed=-48.97 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -885.44 ± 0.06 | kcal/mol | Ccb | Cox, 1961 | Corresponding ΔfHºliquid = -46.18 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -885.25 ± 0.14 | kcal/mol | Ccb | Andon, Biddiscombe, et al., 1960 | Corresponding ΔfHºliquid = -46.37 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -889.4 | kcal/mol | Ccb | Pushin, 1954 | Author's hf298_condensed=-44.4 kcal/mol; Corresponding ΔfHºliquid = -42.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -885.37 | kcal/mol | Ccb | Badoche, 1941 | Author's hf298_condensed=-48.97 kcal/mol; Corresponding ΔfHºliquid = -46.25 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -883.0 | kcal/mol | Ccb | Barker, 1925 | Author was aware that data differs from previously reported values; Corresponding ΔfHºliquid = -48.6 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 50.810 | cal/mol*K | N/A | Andon, Counsell, et al., 1967 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 53.760 | 298.15 | Andon, Counsell, et al., 1967 | T = 10 to 400 K.; DH |
| 52.80 | 93. | Rastorguev and Ganiev, 1967 | T = 293 to 373 K.; DH |
| 52.29 | 298. | Tschamler and Krischai, 1951 | DH |
| 51.79 | 283. | Bramley, 1916 | Mean 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- + =
By formula: C7H7O- + H+ = C7H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 348.2 ± 1.2 | kcal/mol | CIDC | Angel and Ervin, 2006 | gas phase; B |
| ΔrH° | 349.5 ± 2.1 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrH° | 350.7 ± 2.3 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 342.7 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrG° | 343.8 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; B |
+
= (
•
)
By formula: Br- + C7H8O = (Br- • C7H8O)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 20.6 ± 1.8 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 23. | cal/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 10.9 ± 1.0 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 10.9 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
+
=
+
By formula: C9H10O2 + H2O = C7H8O + C2H4O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -4.39 ± 0.14 | kcal/mol | Cm | Sunner, 1957 | liquid 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 ± 0.02 | eV | N/A | N/A | L |
Proton affinity at 298K
| Proton affinity (kcal/mol) | Reference | Comment |
|---|---|---|
| 201. ± 2. | van Beelen, Koblenz, et al., 2004 | T = 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., 2004 | T = 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 ± 0.11 | EI | Selim, Fahmey, et al., 1991 | LL |
| 8.29 ± 0.02 | S | Oikawa, Abe, et al., 1985 | LBLHLM |
| 8.23 | EI | Russell, Freiser, et al., 1983 | LBLHLM |
| 8.52 ± 0.05 | EI | Pignataro, Foffani, et al., 1966 | RDSH |
| 8.98 | EI | Crable and Kearns, 1962 | RDSH |
| 8.41 | PE | Palmer, Moyes, et al., 1979 | Vertical value; LLK |
| 8.52 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C6H5+ | 14.60 ± 0.10 | ? | EI | Selim, Fahmey, et al., 1990 | LL |
| C6H7+ | 11.37 | ? | EI | Russell, Freiser, et al., 1983 | LBLHLM |
| C7H7+ | 11.28 ± 0.05 | OH | EI | Selim, Fahmey, et al., 1990 | LL |
| C7H7O+ | 11.17 | H | EI | Russell, Freiser, et al., 1983 | LBLHLM |
| C7H7O+ | 12.3 ± 0.1 | H | EI | Tait, Shannon, et al., 1962 | RDSH |
De-protonation reactions
C7H7O- + =
By formula: C7H7O- + H+ = C7H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 348.2 ± 1.2 | kcal/mol | CIDC | Angel and Ervin, 2006 | gas phase; B |
| ΔrH° | 349.5 ± 2.1 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrH° | 350.7 ± 2.3 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 342.7 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrG° | 343.8 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas 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
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions T Temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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