p-Cresol

Formula: C₇H₈O
Molecular weight: 108.1378
IUPAC Standard InChI: InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
IUPAC Standard InChIKey: IWDCLRJOBJJRNH-UHFFFAOYSA-N
CAS Registry Number: 106-44-5
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Other names: Phenol, 4-methyl-; p-Hydroxytoluene; p-Kresol; p-Methylhydroxybenzene; p-Methylphenol; p-Oxytoluene; p-Toluol; p-Tolyl alcohol; 1-Hydroxy-4-methylbenzene; 4-Cresol; 4-Hydroxytoluene; 4-Methylphenol; 1-Methyl-4-hydroxybenzene; Paracresol; Cresol, para; Paramethyl phenol; Rcra waste number U052; p-Cresylic acid; Cresol,p-; Phenol, 4-methyI; NSC 3696; 4-methylphenol ( p-cresol); p-Cresol (4-methylphenol)
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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	-29.94 ± 0.36	kcal/mol	Ccb	Cox, 1961	ALS
Δ_fH°_gas	-29.97 ± 0.36	kcal/mol	Ccb	Andon, Biddiscombe, et al., 1960	ALS

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
9.348	50.	Kudchadker S.A., 1978	Selected entropies and heat capacities are in close agreement with statistical values calculated by [ Green J.H.S., 1962] except for S(298.15 K). This value is 3.1 J/mol*K greater than the calculated by [ Green J.H.S., 1962].; GT
12.26	100.
16.35	150.
20.73	200.
27.522	273.15
29.869	298.15
30.041	300.
38.903	400.
46.372	500.
52.409	600.
57.306	700.
61.348	800.
64.732	900.
67.600	1000.
70.048	1100.
72.149	1200.
73.960	1300.
75.526	1400.
76.886	1500.

Condensed phase thermochemistry data

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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	-46.1	kcal/mol	Ccb	Pushin, 1954	Author's hf298_condensed=-48.3 kcal/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-885.5	kcal/mol	Ccb	Pushin, 1954	Author's hf298_condensed=-48.3 kcal/mol; Corresponding Δ_fHº_liquid = -46.1 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	-47.61	kcal/mol	Ccb	Cox, 1961	ALS
Δ_fH°_solid	-47.64 ± 0.36	kcal/mol	Ccb	Andon, Biddiscombe, et al., 1960	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-884.02 ± 0.07	kcal/mol	Ccb	Cox, 1961	Corresponding Δ_fHº_solid = -47.60 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-883.99 ± 0.16	kcal/mol	Ccb	Andon, Biddiscombe, et al., 1960	Corresponding Δ_fHº_solid = -47.63 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-885.0	kcal/mol	Ccb	Barker, 1925	Author was aware that data differs from previously reported values; Corresponding Δ_fHº_solid = -46.6 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	39.990	cal/mol*K	N/A	Andon, Counsell, et al., 1967	DH

Constant pressure heat capacity of solid

C_p,solid (cal/mol*K)	Temperature (K)	Reference	Comment
39.08	298.15	Meva'a and Lichanot, 1990	T = 173 to 353 K. Cp(c) = 145.401 + 0.616T + 3.728x10-3T2 + 2.145x10-5T3 J/molK (-100 to 22 C). Cp(liq) = 232.122 + 0.178T J/molK (40 to 80 C).; DH
52.827	298.15	Nichols and Wads, 1975	DH
35.911	298.15	Andon, Counsell, et al., 1967	T = 10 to 400 K.; DH
54.06	313.	Rastorguev and Ganiev, 1967	T = 313 to 373 K.; DH

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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

+ p-Cresol = ( • )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	25.6 ± 2.0	kcal/mol	TDEq	Cummings, French, et al., 1977	gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B,M
Δ_rH°	25.9	kcal/mol	PHPMS	Paul and Kebarle, 1990	gas phase; Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	25.	cal/mol*K	N/A	Paul and Kebarle, 1990	gas phase; Entropy change calculated or estimated; M
Δ_rS°	26.7	cal/mol*K	PHPMS	Cummings, French, et al., 1977	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	17.9 ± 2.0	kcal/mol	TDEq	Cummings, French, et al., 1977	gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B

Free energy of reaction

Δ_rG° (kcal/mol)	T (K)	Method	Reference	Comment
15.3	423.	PHPMS	Paul and Kebarle, 1990	gas phase; Entropy change calculated or estimated; M
16.6	300.	PHPMS	Cummings, French, et al., 1977	gas phase; M

C₇H₇O^- + = p-Cresol

By formula: C₇H₇O^- + H⁺ = C₇H₈O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	350.2 ± 2.1	kcal/mol	G+TS	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale; B
Δ_rH°	350.2 ± 2.1	kcal/mol	G+TS	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
Δ_rH°	351.6 ± 2.3	kcal/mol	G+TS	Kebarle and McMahon, 1977	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	343.4 ± 2.0	kcal/mol	IMRE	Fujio, McIver, et al., 1981	gas phase; value altered from reference due to change in acidity scale; B
Δ_rG°	343.4 ± 2.0	kcal/mol	IMRE	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B
Δ_rG°	344.7 ± 2.0	kcal/mol	IMRE	Kebarle and McMahon, 1977	gas phase; B

+ p-Cresol = ( • )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	20.3 ± 1.8	kcal/mol	IMRE	Paul and Kebarle, 1990	gas phase; ΔGaff at 423 K; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	23.	cal/mol*K	N/A	Paul and Kebarle, 1990	gas phase; Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	10.6 ± 1.0	kcal/mol	IMRE	Paul and Kebarle, 1990	gas phase; ΔGaff at 423 K; B

Free energy of reaction

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

+ p-Cresol = ( • )

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	16.4 ± 1.8	kcal/mol	IMRE	Paul and Kebarle, 1990	gas phase; ΔGaff at 423 K; B,M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	21.	cal/mol*K	N/A	Paul and Kebarle, 1990	gas phase; Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	7.5 ± 1.0	kcal/mol	IMRE	Paul and Kebarle, 1990	gas phase; ΔGaff at 423 K; B

Free energy of reaction

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

p-Cresol + = 2

By formula: C₇H₈O + C₁₅H₂₄O = 2C₁₁H₁₆O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-2.3 ± 0.43	kcal/mol	Eqk	Nesterova, Verevkin, et al., 1985	liquid phase; ALS

p-Cresol + =

By formula: C₇H₈O + C₄H₈ = C₁₁H₁₆O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	15.0 ± 0.67	kcal/mol	Eqk	Verevkin, Nesterova, et al., 1984	gas phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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]

Meva'a and Lichanot, 1990
Meva'a, L.M.; Lichanot, A., Proprietes thermodynamiques en phase condensee des ortho, meta et para fluorotoluene, cresol et toluidine, Thermochim. Acta, 1990, 158, 335-345. [all data]

Nichols and Wads, 1975
Nichols, N.; Wads, I., Thermochemistry of solutions of biochemical model compounds. 3. Some benzene derivatives in aqueous solution, J. Chem. Thermodynam., 1975, 7, 329-336. [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]

Cummings, French, et al., 1977
Cummings, J.B.; French, M.A.; Kebarle, P., Effect of charge delocalization on hydrogen bonding to negative ions and solvation of negative ions. Substituted phenols and phenoxide ions, J. Am. Chem. Soc., 1977, 99, 6999. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [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]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [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]

Verevkin, Nesterova, et al., 1984
Verevkin, S.P.; Nesterova, T.N.; Rozhnov, A.M., The equilibrium in the dealkylation of o-t-butyl-p-cresol, Russ. J. Phys. Chem. (Engl. Transl.), 1984, 58, 284. [all data]

Notes

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

Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
C_p,solid	Constant pressure heat capacity of solid
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
T	Temperature
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
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