p-Cresol

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Phase change data

Go To: Top, Gas phase ion energetics data, Ion clustering 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil475.0 ± 0.9KAVGN/AAverage of 13 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus307. ± 2.KAVGN/AAverage of 16 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple307.94KN/AAndon, Counsell, et al., 1967Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Tc704.6KN/ADelaunois, 1968Uncertainty assigned by TRC = 0.4 K; TRC
Tc704.55KN/AAmbrose, 1963Uncertainty assigned by TRC = 0.3 K; TRC
Tc699.KN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 3. K; TRC
Tc699.2KN/ARadice, 1899Uncertainty assigned by TRC = 5. K; TRC
Quantity Value Units Method Reference Comment
Pc40.70barN/ADelaunois, 1968Uncertainty assigned by TRC = 0.5884 bar; TRC
Pc45.5963barN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 3.0398 bar; TRC
Pc51.4731barN/AHerz and Neukirch, 1923Uncertainty assigned by TRC = 0.8106 bar; TRC
Quantity Value Units Method Reference Comment
Δvap46.61kJ/molCGlaser and Ruland, 1957ALS
Quantity Value Units Method Reference Comment
Δsub73.1 ± 0.6kJ/molCRichard, Bernardes, et al., 2007AC
Δsub73.9kJ/molN/ACox, 1961DRB
Δsub73.9 ± 1.5kJ/molVAndon, Biddiscombe, et al., 1960ALS
Δsub73.9kJ/molN/AAndon, Biddiscombe, et al., 1960DRB

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
62.0323.AStephenson and Malanowski, 1987Based on data from 308. to 393. K.; AC
55.4400.AStephenson and Malanowski, 1987Based on data from 385. to 477. K.; AC
49.2478.AStephenson and Malanowski, 1987Based on data from 463. to 533. K.; AC
46.0538.AStephenson and Malanowski, 1987Based on data from 523. to 635. K.; AC
55.6398.A,GS,EBStephenson and Malanowski, 1987Based on data from 383. to 473. K. See also Andon, Biddiscombe, et al., 1960, 2 and Kkykj and Repas, 1973.; AC
51.3446.N/AGoldblum, Martin, et al., 1947Based on data from 419. to 474. K.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
401.20 to 475.034.140931498.579-112.6Dreisbach and Shrader, 1949Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Reference Comment
73.9 ± 1.5290.Andon, Biddiscombe, et al., 1960, 2Based on data from 273. to 307. K. See also Cox and Pilcher, 1970.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Method Reference Comment
11.800307.35N/AMeva'a and Lichanot, 1990DH
11.887309.0N/APoeti, Fanelli, et al., 1982DH
12.707307.94N/AAndon, Counsell, et al., 1967, 2DH
12.6308.8DSCRichard, Bernardes, et al., 2007AC
8.58307.6DSCJamróz, Palczewska-Tulinska, et al., 1998AC
12.72307.9N/ADomalski and Hearing, 1996AC
11.8307.4N/AMeva'a and Lichanot, 1990AC
12.247309.N/AEykman, 1889DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
38.307.35Meva'a and Lichanot, 1990DH
38.47309.0Poeti, Fanelli, et al., 1982DH
41.26307.94Andon, Counsell, et al., 1967, 2DH
39.6309.Eykman, 1889DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Gas phase ion energetics data

Go To: Top, Phase change data, Ion clustering data, References, Notes

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)8.34 ± 0.03eVN/AN/AL

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
814. ± 8.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) (kJ/mol) Reference Comment
782. ± 8.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
8.31 ± 0.08EISelim, Fahmey, et al., 1991LL
8.13EIRussell, Freiser, et al., 1983LBLHLM
8.34EIJohnstone and Mellon, 1973LLK
8.97EICrable and Kearns, 1962RDSH
8.35PEPalmer, Moyes, et al., 1979Vertical value; LLK
8.38PEKobayashi and Nagakura, 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H5+15.69 ± 0.08?EISelim, Fahmey, et al., 1990LL
C6H7+11.50?EIRussell, Freiser, et al., 1983LBLHLM
C7H7+11.67 ± 0.08OHEISelim, Fahmey, et al., 1990LL
C7H7O+11.13HEIRussell, Freiser, et al., 1983LBLHLM
C7H7O+12.4 ± 0.1HEITait, Shannon, et al., 1962RDSH

De-protonation reactions

C7H7O- + Hydrogen cation = p-Cresol

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Δr1465. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1465. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr1471. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr1437. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1437. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Δr1442. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

Ion clustering data

Go To: Top, Phase change 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

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

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

Quantity Value Units Method Reference Comment
Δr84.9 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr96.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr44.4 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
44.4423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

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

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

Quantity Value Units Method Reference Comment
Δr107. ± 8.4kJ/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B,M
Δr108.kJ/molPHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr100.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Δr112.J/mol*KPHPMSCummings, French, et al., 1977gas phase; M
Quantity Value Units Method Reference Comment
Δr74.9 ± 8.4kJ/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B

Free energy of reaction

ΔrG° (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

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

By formula: I- + C7H8O = (I- • C7H8O)

Quantity Value Units Method Reference Comment
Δr68.6 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr88.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr31. ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
31.423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

References

Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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. [all data]

Delaunois, 1968
Delaunois, C., Effect of the Filling Rate of a Reactor on the Vapor Tension and the Temperature at the Beginning of Cracking of Phenols at High Pressures, Ann. Mines Belg., 1968, No. 1, 9-16. [all data]

Ambrose, 1963
Ambrose, D., Critical Temperatures of Some Phenols and Other Organic Compounds, Trans. Faraday Soc., 1963, 59, 1988. [all data]

Glaser and Ruland, 1957
Glaser, F.; Ruland, H., Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen, Chem. Ing. Techn., 1957, 29, 772. [all data]

Radice, 1899
Radice, G., , Ph. D. Thesis, Univ. of Geneve, 1899. [all data]

Herz and Neukirch, 1923
Herz, W.; Neukirch, E., On Knowldge of the Critical State, Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1923, 104, 433-50. [all data]

Richard, Bernardes, et al., 2007
Richard, Laurence S.; Bernardes, Carlos E.S.; Diogo, Hermínio P.; Leal, João P.; Minas da Piedade, Manuel E., Energetics of Cresols and of Methylphenoxyl Radicals, J. Phys. Chem. A, 2007, 111, 35, 8741-8748, https://doi.org/10.1021/jp073515m . [all data]

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]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Andon, Biddiscombe, et al., 1960, 2
Andon, R.J.L.; Biddiscombe, D.P.; Cox, J.D.; Handley, R.; Harrop, D.; Herington, E.F.G.; Martin, J.F., 1009. Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols, J. Chem. Soc., 1960, 5246, https://doi.org/10.1039/jr9600005246 . [all data]

Kkykj and Repas, 1973
Kkykj, J.; Repas, M., Petrochemia, 1973, 13, 179. [all data]

Goldblum, Martin, et al., 1947
Goldblum, K.B.; Martin, R.W.; Young, R.B., Vapor Pressure Data for Phenols, Ind. Eng. Chem., 1947, 39, 11, 1474-1476, https://doi.org/10.1021/ie50455a017 . [all data]

Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A., Vapor Pressure--Temperature Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054 . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [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]

Poeti, Fanelli, et al., 1982
Poeti, G.; Fanelli, E.; Braghetti, M., A differential scanning calorimetric study of some phenol derivatives, J. Therm. Anal., 1982, 24(2), 273-279. [all data]

Andon, Counsell, et al., 1967, 2
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]

Jamróz, Palczewska-Tulinska, et al., 1998
Jamróz, Malgorzata E.; Palczewska-Tulinska, Marcela; Wyrzykowska-Stankiewicz, Danuta; Szafranski, Andrzej M.; Polaczek, Jerzy; Dobrowolski, Jan Cz.; Jamróz, Michal H.; Mazurek, Aleksander P., The urea--phenol(s) systems, Fluid Phase Equilibria, 1998, 152, 2, 307-326, https://doi.org/10.1016/S0378-3812(98)90206-0 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Eykman, 1889
Eykman, J.F., Zur kryoskopischen Molekulargewichtsbestimmung, Z. Physik. Chem., 1889, 4, 497-519. [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]

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]

Johnstone and Mellon, 1973
Johnstone, R.A.W.; Mellon, F.A., Effects of induction and resonance in the calculation of ionization potentials of substituted benzenes by perturbation molecular orbital theory, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 36. [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]

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]

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]

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]


Notes

Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, References