Phenol, 2-methyl-

Formula: C₇H₈O
Molecular weight: 108.1378
IUPAC Standard InChI: InChI=1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3
IUPAC Standard InChIKey: QWVGKYWNOKOFNN-UHFFFAOYSA-N
CAS Registry Number: 95-48-7
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: o-Cresol; o-Hydroxytoluene; o-Methylphenol; o-Methylphenylol; o-Oxytoluene; 1-Hydroxy-2-methylbenzene; 2-Cresol; 2-Hydroxytoluene; 2-Methylphenol; Orthocresol; o-Kresol; Rcra waste number U052; o-Cresylic acid; 1-Methyl-2-hydroxybenzene; NSC 23076; o-Toluol
Permanent link for this species. Use this link for bookmarking this species for future reference.
Information on this page:
Other data available:
Data at other public NIST sites:
- Gas Phase Kinetics Database
Options:
- Switch to calorie-based units

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References, Notes

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-128.3 ± 0.88	kJ/mol	Ccb	Cox, 1961	ALS
Δ_fH°_gas	-128.6 ± 0.92	kJ/mol	Ccb	Andon, Biddiscombe, et al., 1960	ALS

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
38.22	50.	Kudchadker S.A., 1978	Selected entropy values at 298.15 and 400 K are lower than the experimental ones by 2.2 and 2.1 J/molK, respectively. The discrepancy is close to the experimental uncertainty. The same entropy values calculated by [ Green J.H.S., 1962] are greater than the observed by 2.8 and 3.9 J/molK.; GT
59.18	100.
75.09	150.
91.26	200.
117.84	273.15
127.30	298.15
128.00	300.
164.31	400.
195.29	500.
220.43	600.
240.85	700.
257.68	800.
271.77	900.
283.70	1000.
293.87	1100.
302.60	1200.
310.11	1300.
316.61	1400.
322.25	1500.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References, Notes

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
Δ_fH°_liquid	-202.	kJ/mol	Ccb	Pushin, 1954	Author's hf298_condensed=-50.6 kcal/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-3696.	kJ/mol	Ccb	Pushin, 1954	Author's hf298_condensed=-50.6 kcal/mol; Corresponding Δ_fHº_liquid = -202. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	-204.3	kJ/mol	Ccb	Cox, 1961	ALS
Δ_fH°_solid	-204.6 ± 0.92	kJ/mol	Ccb	Andon, Biddiscombe, et al., 1960	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-3693.6 ± 0.42	kJ/mol	Ccb	Cox, 1961	Corresponding Δ_fHº_solid = -204.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-3693.3 ± 1.0	kJ/mol	Ccb	Andon, Biddiscombe, et al., 1960	Corresponding Δ_fHº_solid = -204.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-3697.	kJ/mol	Ccb	Barker, 1925	Author was aware that data differs from previously reported values; Corresponding Δ_fHº_solid = -200. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	165.44	J/mol*K	N/A	Andon, Counsell, et al., 1967	DH

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
233.6	313.	Rastorguev and Ganiev, 1967	T = 313 to 373 K.; DH
225.9	283.	Bramley, 1916	Mean value, 0 to 20 C.; DH

Constant pressure heat capacity of solid

C_p,solid (J/mol*K)	Temperature (K)	Reference	Comment
154.56	298.15	Andon, Counsell, et al., 1967	T = 10 to 400 K.; DH

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Henry's Law data, References, Notes

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

+ Phenol, 2-methyl- = ( • )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	86.2 ± 7.5	kJ/mol	IMRE	Paul and Kebarle, 1990	gas phase; ΔGaff at 423 K; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	96.	J/mol*K	N/A	Paul and Kebarle, 1990	gas phase; Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	45.6 ± 4.2	kJ/mol	IMRE	Paul and Kebarle, 1990	gas phase; ΔGaff at 423 K; B

Free energy of reaction

Δ_rG° (kJ/mol)	T (K)	Method	Reference	Comment
45.6	423.	PHPMS	Paul and Kebarle, 1990	gas phase; Entropy change calculated or estimated; M

C₇H₇O^- + = Phenol, 2-methyl-

By formula: C₇H₇O^- + H⁺ = C₇H₈O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1462. ± 9.2	kJ/mol	G+TS	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale; B
Δ_rH°	1465. ± 12.	kJ/mol	G+TS	Kebarle and McMahon, 1977	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1431. ± 8.4	kJ/mol	IMRE	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale; B
Δ_rG°	1434. ± 8.4	kJ/mol	IMRE	Kebarle and McMahon, 1977	gas phase; B

+ Phenol, 2-methyl- = +

By formula: C₁₅H₂₄O + C₇H₈O = C₁₁H₁₆O + C₁₁H₁₆O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	2.5 ± 3.5	kJ/mol	Eqk	Nesterova, Verevkin, et al., 1985	liquid phase; ALS

Henry's Law data

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

Data compiled by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

k°_H (mol/(kg*bar))	d(ln(k_H))/d(1/T) (K)	Method	Reference	Comment
1200.		Q	N/A	missing citation give several references for the Henry's law constants but don't assign them to specific species. Value at T = 293. K.
820.		X	N/A
260.	4600.	X	N/A
830.		X	N/A	Value given here as quoted by missing citation.
820.	7300.	M	N/A	It is assumed here that the thermodynamic data in missing citation refers to the units [mol/dm³] and [atm] as standard states.

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Notes

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]

Kudchadker S.A., 1978
Kudchadker S.A., Ideal gas thermodynamic properties of phenol and cresols, J. Phys. Chem. Ref. Data, 1978, 7, 417-423. [all data]

Green J.H.S., 1962
Green J.H.S., Normal frequencies, thermodynamic properties and equilibrium of the cresols, Chem. Ind. (London), 1962, 1575-1576. [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]

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]

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]

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]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References

Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
C_p,solid	Constant pressure heat capacity of solid
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
T	Temperature
d(ln(k_H))/d(1/T)	Temperature dependence parameter for Henry's Law constant
k°_H	Henry's Law constant at 298.15K
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_rS°	Entropy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
Customer support for NIST Standard Reference Data products.