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p-Cresol

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas-125.3 ± 1.5kJ/molCcbCox, 1961ALS
Deltafgas-125.4 ± 1.5kJ/molCcbAndon, Biddiscombe, et al., 1960ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
39.1150.Kudchadker S.A., 1978Selected 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
51.31100.
68.39150.
86.75200.
115.15273.15
124.97298.15
125.69300.
162.77400.
194.02500.
219.28600.
239.77700.
256.68800.
270.84900.
282.841000.
293.081100.
301.871200.
309.451300.
316.001400.
321.691500.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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
Deltafliquid-193.kJ/molCcbPushin, 1954Author's hf298_condensed=-48.3 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3705.kJ/molCcbPushin, 1954Author's hf298_condensed=-48.3 kcal/mol; Corresponding «DELTA»fliquid = -193. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
Deltafsolid-199.2kJ/molCcbCox, 1961ALS
Deltafsolid-199.3 ± 1.5kJ/molCcbAndon, Biddiscombe, et al., 1960ALS
Quantity Value Units Method Reference Comment
Deltacsolid-3698.7 ± 0.3kJ/molCcbCox, 1961Corresponding «DELTA»fsolid = -199.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-3698.6 ± 0.67kJ/molCcbAndon, Biddiscombe, et al., 1960Corresponding «DELTA»fsolid = -199.3 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-3703.kJ/molCcbBarker, 1925Author was aware that data differs from previously reported values; Corresponding «DELTA»fsolid = -195. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar167.32J/mol*KN/AAndon, Counsell, et al., 1967DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
163.5298.15Meva'a and Lichanot, 1990T = 173 to 353 K. Cp(c) = 145.401 + 0.616T + 3.728x10-3T2 + 2.145x10-5T3 J/mol*K (-100 to 22 C). Cp(liq) = 232.122 + 0.178T J/mol*K (40 to 80 C).; DH
221.03298.15Nichols and Wads, 1975DH
150.25298.15Andon, Counsell, et al., 1967T = 10 to 400 K.; DH
226.2313.Rastorguev and Ganiev, 1967T = 313 to 373 K.; DH

Reaction thermochemistry data

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

Chlorine anion + p-Cresol = (Chlorine anion bullet p-Cresol)

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

Quantity Value Units Method Reference Comment
Deltar107. ± 8.4kJ/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B,M
Deltar108.kJ/molPHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar100.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Deltar112.J/mol*KPHPMSCummings, French, et al., 1977gas phase; M
Quantity Value Units Method Reference Comment
Deltar74.9 ± 8.4kJ/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
64.0423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
69.5300.PHPMSCummings, French, et al., 1977gas phase; M

C7H7O- + Hydrogen cation = p-Cresol

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Deltar1465. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1465. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar1471. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar1437. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1437. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar1442. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

Bromine anion + p-Cresol = (Bromine anion bullet p-Cresol)

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

Quantity Value Units Method Reference Comment
Deltar84.9 ± 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
Deltar44.4 ± 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
44.4423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

Iodide + p-Cresol = (Iodide bullet p-Cresol)

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

Quantity Value Units Method Reference Comment
Deltar68.6 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar88.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar31. ± 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
31.423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

p-Cresol + Butylated Hydroxytoluene = 2Phenol, 2-(1,1-dimethylethyl)-4-methyl-

By formula: C7H8O + C15H24O = 2C11H16O

Quantity Value Units Method Reference Comment
Deltar-9.7 ± 1.8kJ/molEqkNesterova, Verevkin, et al., 1985liquid phase; ALS

p-Cresol + 1-Propene, 2-methyl- = Phenol, 2-(1,1-dimethylethyl)-4-methyl-

By formula: C7H8O + C4H8 = C11H16O

Quantity Value Units Method Reference Comment
Deltar62.7 ± 2.8kJ/molEqkVerevkin, Nesterova, et al., 1984gas phase; ALS

References

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

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