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Phenol, 2-methyl-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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-30.67 ± 0.21kcal/molCcbCox, 1961ALS
Deltafgas-30.74 ± 0.22kcal/molCcbAndon, Biddiscombe, et al., 1960ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
9.13550.Kudchadker S.A., 1978Selected entropy values at 298.15 and 400 K are lower than the experimental ones by 2.2 and 2.1 J/mol*K, 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/mol*K.; GT
14.14100.
17.95150.
21.81200.
28.164273.15
30.425298.15
30.593300.
39.271400.
46.675500.
52.684600.
57.565700.
61.587800.
64.955900.
67.8061000.
70.2371100.
72.3231200.
74.1181300.
75.6721400.
77.0201500.

Condensed phase 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:
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-48.3kcal/molCcbPushin, 1954Author's hf298_condensed=-50.6 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-883.3kcal/molCcbPushin, 1954Author's hf298_condensed=-50.6 kcal/mol; Corresponding «DELTA»fliquid = -48.3 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
Deltafsolid-48.84kcal/molCcbCox, 1961ALS
Deltafsolid-48.91 ± 0.22kcal/molCcbAndon, Biddiscombe, et al., 1960ALS
Quantity Value Units Method Reference Comment
Deltacsolid-882.79 ± 0.10kcal/molCcbCox, 1961Corresponding «DELTA»fsolid = -48.83 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-882.72 ± 0.24kcal/molCcbAndon, Biddiscombe, et al., 1960Corresponding «DELTA»fsolid = -48.90 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-883.7kcal/molCcbBarker, 1925Author was aware that data differs from previously reported values; Corresponding «DELTA»fsolid = -47.9 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar39.541cal/mol*KN/AAndon, Counsell, et al., 1967DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
55.83313.Rastorguev and Ganiev, 1967T = 313 to 373 K.; DH
53.99283.Bramley, 1916Mean value, 0 to 20 C.; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
36.941298.15Andon, Counsell, et al., 1967T = 10 to 400 K.; DH

Phase change 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:
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
Tboil464.3 ± 0.6KAVGN/AAverage of 11 out of 12 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus304. ± 1.KAVGN/AAverage of 15 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple304.20KN/AAndon, Counsell, et al., 1967, 2Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Tc697.6KN/ADelaunois, 1968Uncertainty assigned by TRC = 0.4 K; TRC
Tc697.55KN/AAmbrose, 1963Uncertainty assigned by TRC = 0.23 K; TRC
Tc695.15KN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 2. K; TRC
Tc695.5KN/ARadice, 1899Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Pc41.15atmN/ADelaunois, 1968Uncertainty assigned by TRC = 0.3871 atm; TRC
Pc48.000atmN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 3.0000 atm; TRC
Pc49.4000atmN/AHerz and Neukirch, 1923Uncertainty assigned by TRC = 0.6999 atm; TRC
Quantity Value Units Method Reference Comment
Deltavap10.73kcal/molCGlaser and Ruland, 1957ALS
Quantity Value Units Method Reference Comment
Deltasub17.6 ± 0.1kcal/molCRichard, Bernardes, et al., 2007AC
Deltasub18.2kcal/molN/ACox, 1961DRB
Deltasub18.17 ± 0.18kcal/molVAndon, Biddiscombe, et al., 1960ALS
Deltasub18.2kcal/molN/AAndon, Biddiscombe, et al., 1960DRB

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
14.0319.AStephenson and Malanowski, 1987Based on data from 304. - 409. K.; AC
12.0414.AStephenson and Malanowski, 1987Based on data from 399. - 470. K.; AC
11.0478.AStephenson and Malanowski, 1987Based on data from 463. - 526. K.; AC
10.5532.AStephenson and Malanowski, 1987Based on data from 517. - 630. K.; AC
12.3398.GS,EBStephenson and Malanowski, 1987Based on data from 383. - 473. K. See also Andon, Biddiscombe, et al., 1960, 2 and Kkykj and Repas, 1973.; AC
11.5438.N/AGoldblum, Martin, et al., 1947Based on data from 415. - 462. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
393.37 - 464.103.962041391.332-112.974Dreisbach and Shrader, 1949Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
17.9288.AStephenson and Malanowski, 1987Based on data from 273. - 303. K.; AC
18.2 ± 0.2288.N/AAndon, Biddiscombe, et al., 1960, 2Based on data from 273. - 303. K. See also Cox and Pilcher, 1970.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Method Reference Comment
3.5373304.05N/AMeva'a and Lichanot, 1990DH
3.3313303.0N/APoeti, Fanelli, et al., 1982DH
3.7811304.20N/AAndon, Counsell, et al., 1967DH
3.54305.4DSCRichard, Bernardes, et al., 2007AC
3.80304.1DSCJamróz, Palczewska-Tulinska, et al., 1998AC
3.781304.2N/ADomalski and Hearing, 1996AC
3.54304.1N/AMeva'a and Lichanot, 1990AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
12.304.05Meva'a and Lichanot, 1990DH
10.99303.0Poeti, Fanelli, et al., 1982DH
12.43304.20Andon, Counsell, et al., 1967DH

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:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), 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

Bromine anion + Phenol, 2-methyl- = (Bromine anion bullet Phenol, 2-methyl-)

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

Quantity Value Units Method Reference Comment
Deltar20.6 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar23.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar10.9 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
10.9423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

C7H7O- + Hydrogen cation = Phenol, 2-methyl-

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Deltar349.5 ± 2.2kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar350.2 ± 2.9kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar342.0 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar342.7 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

Phenol, 4,6-di(1,1-dimethylethyl)-2-methyl- + Phenol, 2-methyl- = Phenol, 2-(1,1-dimethylethyl)-6-methyl- + Phenol, 4-(1,1-dimethylethyl)-2-methyl-

By formula: C15H24O + C7H8O = C11H16O + C11H16O

Quantity Value Units Method Reference Comment
Deltar0.60 ± 0.84kcal/molEqkNesterova, Verevkin, et al., 1985liquid phase; ALS

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-6819
NIST MS number 228359

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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]

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]

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. [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]

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]

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]

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, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References