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Cyclohexane, methyl-

• Formula: C₇H₁₄
• Molecular Weight: 98.19
• CAS Registry Number: 108-87-2
• Chemical Structure:
  This structure is also available as a 2d Mol file or as a computed 3d Mol file.
• Other Names: Cyclohexylmethane; Hexahydrotoluene; Methylcyclohexane; Sextone B; Toluene hexahydride; Hexahydroxytoluene; Metylocykloheksan; Toluene, hexahydro-; UN 2296
• Gas phase thermochemistry data
• Condensed phase thermochemistry data
• Phase change data
• Reaction thermochemistry data
• Henry's Law data
• Gas phase ion energetics data
• Gas Phase IR Spectrum
• Mass Spectrum
• References
• Notes / Error Report
• Switch to calorie-based units

Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Gas Phase IR Spectrum, Mass Spectrum, References, Notes / Error Report

Data compiled as indicated in comments:
ALS - H.Y. Afeefy, J.F. Liebman, and S.E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, V.S. Yungman, director

Constant pressure heat capacity of gas.

Constant pressure heat capacity of gas.

Condensed phase thermochemistry data

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Data compiled as indicated in comments:
ALS - H.Y. Afeefy, J.F. Liebman, and S.E. Stein
DH - E.S. Domalski and E.D. Hearing

Constant pressure heat capacity of liquid.

Phase change data

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Data compiled as indicated in comments:
BS - R.L. Brown and S.E. Stein
DH - E.S. Domalski and E.D. Hearing
ALS - H.Y. Afeefy, J.F. Liebman, and S.E. Stein

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH° = A exp(-βT_r) (1 - T_r)^β
    Δ_vapH° = Enthalpy of vaporization (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Enthalpy of fusion

Entropy of fusion

Reaction thermochemistry data

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Data compiled by: H.Y. Afeefy, J.F. Liebman, and S.E. Stein

Individual Reactions

+  =

Quantity Value Units Method Reference Comment ΔrH° -119.5 ± 0.65 kJ/mol Chyd Rogers, Crooks, et al., 1987 liquid phase ΔrH° -116.1 ± 0.54 kJ/mol Chyd Turner and Garner, 1958 liquid phase; solvent: Acetic acid ΔrH° -116.1 ± 0.54 kJ/mol Eqk Turner and Garner, 1957 liquid phase; solvent: Acetic acid ΔrH° -120.1 ± 0.3 kJ/mol Chyd Turner and Garner, 1957, 2 liquid phase; solvent: Acetic acid

+  =

Quantity Value Units Method Reference Comment ΔrH° -111.4 ± 0.37 kJ/mol Chyd Rogers, Crooks, et al., 1987 liquid phase ΔrH° -106.3 ± 0.46 kJ/mol Chyd Turner and Garner, 1958 liquid phase; solvent: Acetic acid ΔrH° -106.3 ± 0.46 kJ/mol Chyd Turner and Garner, 1957 liquid phase; solvent: Acetic acid

2  +  =

Quantity Value Units Method Reference Comment ΔrH° -387. ± 0.4 kJ/mol Chyd Roth, Adamczak, et al., 1991 liquid phase

Henry's Law data

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Data compiled by: R. Sander

Henry's Law constant (water solution)

    k°_H = Henry's law constant for solubility in water at 298.15 K (mol/kg*bar)

Gas phase ion energetics data

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Data evaluated as indicated in comments:
L - S.G. Lias

Data compiled as indicated in comments:
LL - S.G. Lias and J.F. Liebman
LBLHLM - S.G. Lias, J.E. Bartmess, J.F. Liebman, J.L. Holmes, R.D. Levin, and W.G. Mallard
LLK - S.G. Lias, R.D. Levin, and S.A. Kafafi
RDSH - H.M. Rosenstock, K. Draxl, B.W. Steiner, and J.T. Herron

Ionization energy determinations

Appearance energy determinations

Gas Phase IR Spectrum

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Data compiled by: NIST Mass Spec Data Center, S.E. Stein, director

Notice: This spectrum may be better viewed with a Java capable browser.

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Additional Data

View Large Spectrum Image (can be printed in landscape orientation)

Owner	NIST Standard Reference Data Program
Origin	Sadtler Research Labs Under US-EPA Contract
Source reference	No.12 (EPA Vapor Library)

Mass Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Gas Phase IR Spectrum, References, Notes / Error Report

Data compiled by: NIST Mass Spec Data Center, S.E. Stein, director

Notice: This spectrum may be better viewed with a Java capable browser.

For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View Large Spectrum Image (can be printed in landscape orientation)

Owner	NIST Mass Spectrometry Data Center
Origin	NIST Mass Spectrometry Data Center, 1990.
Origin code	NBS
Instrument	HP MSD
Inlet	GC
Instrument IE (eV)	70
Sample temp. (C)	280
Source temp. (C)	240
EPA MS number	118503

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Gas Phase IR Spectrum, Mass Spectrum, Notes / Error Report

Prosen, Johnson, et al., 1946
Prosen, E.J.; Johnson, W.H.; Rossini, F.D., Heats of formation and combustion of the normal alkylcyclopentanes and cyclohexanes and the increment per CH₂ group for several homologous series of hydrocarbons, J. Res. NBS, 1946, 37, 51-56.  [all data]

Beckett C.W., 1947
Beckett C.W., The thermodynamic properties and molecular structure of cyclohexane, methylcyclohexane, ethylcyclohexane, and seven dimethylcyclohexanes, J. Am. Chem. Soc., 1947, 69, 2488-2495.  [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997.  [all data]

Spitzer R., 1946
Spitzer R., The heat capacity of gaseous cyclopentane, cyclohexane and methylcyclohexane, J. Am. Chem. Soc., 1946, 68, 2537-2538.  [all data]

Montgomery J.B., 1942
Montgomery J.B., The heat capacity of organic vapors. IV. Benzene, fluorobenzene, toluene, cyclohexane, methylcyclohexane and cyclohexene, J. Am. Chem. Soc., 1942, 64, 2375-2377.  [all data]

Moore, Renquist, et al., 1940
Moore, G.E.; Renquist, M.L.; Parks, G.S., Thermal data on organic compounds. XX. Modern combustion data for two methylnonanes, methyl ethyl ketone, thiophene and six cycloparaffins, J. Am. Chem. Soc., 1940, 62, 1505-1507.  [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636.  [all data]

Douslin and Huffman, 1946
Douslin, D.R.; Huffman, H.M., The heat capacities, heats of transition, heats of fusion and entropies of cyclopentane, methylcyclopentane and methylcylohexane, J. Am. Chem. Soc., 1946, 68, 173-176.  [all data]

Parks and Huffman, 1930
Parks, G.S.; Huffman, H.M., Thermal data on organic compounds. IX. A study of the effect of unsaturation on the heat capacities, entropies and free energies of some hydrocarbons and other compounds, J. Am. Chem. Soc., 1930, 52, 4381-4391.  [all data]

Shiohama, Ogawa, et al., 1988
Shiohama, Y.; Ogawa, H.; Murakami, S.; Fujihara, I., Excess thermodynamic properties of (cis-decalin or trans-decalin + cyclohexane or methylcyclohexane or cyclooctane) at 298.15 K, J. Chem. Thermodynam., 1988, 20, 1307-1314.  [all data]

Tanaka, 1985
Tanaka, R., Excess heat capacities for mixtures of benzene with cyclopentane, methylcyclohexane, and cyclooctane at 298.15 K, J. Chem. Eng. Data, 1985, 30, 267-269.  [all data]

Grolier, Inglese, et al., 1982
Grolier, J.-P.E.; Inglese, A.; Wilhelm, E., Excess volumes and excess heat capacities of tetrachloroethene + cyclohexane, + methylcyclohexane, + benzene, and + toluene at 298.15 K, J. Chem. Thermodynam., 1982, 14, 523-529.  [all data]

Wilhelm, Grolier, et al., 1979
Wilhelm, E.; Grolier, G.-P.E.; Karbalai Ghassemi, M.H., Molar heat capacity of binary liquid mixtures: 1,2-dichloroethane + cyclohexane and 1,2-dichloroethane + methylcyclohexane, Thermochim. Acta, 1979, 28, 59-69.  [all data]

Holzhauer and Ziegler, 1975
Holzhauer, J.K.; Ziegler, W.T., Temperature dependence of excess thermodynamic properties of n-heptane-toluene, methylcyclohexane-toluene, and n-heptane-methylcyclohexane systems, J. Phys. Chem., 1975, 79(6), 590-604.  [all data]

Hwa and Ziegler, 1966
Hwa, S.C.P.; Ziegler, W.T., Temperature dependence of excess thermodynamic properties of ethanol-methylcyclohexane and ethanol-toluene systems, J. Phys. Chem., 1966, 70(8), 2572-2593.  [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1.  [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300.  [all data]

Daubert, 1996
Daubert, T.E., Vapor-Liquid Critical Properties of Elements and Compounds. 5. Branched Alkanes and Cycloalkanes, J. Chem. Eng. Data, 1996, 41, 365-372.  [all data]

Fuchs and Peacock, 1978
Fuchs, R.; Peacock, L.A., Heats of vaporization of monoalkylcyclohexanes by the gas chromatography-calorimetry method, Can. J. Chem., 1978, 56, 2493-24.  [all data]

Wadso, 1966
Wadso, I., A heat of vaporization calorimeter for work at 25°C and for small amounts of substances, Acta Chem. Scand., 1966, 20, 536.  [all data]

Wadso, 1960
Wadso, I., An adiabatic calorimeter for measuring heats of vaporisation at 25° C, Acta Chem. Scand., 1960, 14, 566-572.  [all data]

Osborne and Ginnings, 1947
Osborne, N.S.; Ginnings, D.C., Measurements of heat of vaporization and heat capacity of a number of hydrocarbons, J. Res. NBS, 1947, 39, 453-477.  [all data]

Mathews, 1926
Mathews, J.H., The accurate measurement of heats of vaporization of liquids, J. Am. Chem. Soc., 1926, 48, 562-576.  [all data]

Zubova, 1901
Zubova, P., Data about heat of combustion of compound cycle structure, Zh. Fiz. Khim., 1901, 33, 708-722.  [all data]

Rogers, Crooks, et al., 1987
Rogers, D.W.; Crooks, E.; Dejroongruang, K., Enthalpies of hydrogenation of the hexenes, J. Chem. Thermodyn., 1987, 19, 1209-1215.  [all data]

Turner and Garner, 1958
Turner, R.B.; Garner, R.H., Heats of hydrogenation. V. Relative stabilities in certain exocyclic-endocyclic olefin pairs, J. Am. Chem. Soc., 1958, 80, 1424-1430.  [all data]

Turner and Garner, 1957
Turner, R.B.; Garner, R.H., Heats of hydrogenation. V. Relative stabilities in certain exocyclic-endocyclic olefin pairs, J. Am. Chem. Soc., 1957, 80, 1424-1430.  [all data]

Turner and Garner, 1957, 2
Turner, R.B.; Garner, R.H., The stability relationship of 1-methyl-cyclopentene and methylenecyclopentane, J. Am. Chem. Soc., 1957, 79, 253.  [all data]

Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R., Die Berechnung von Resonanzenergien; das MM₂ERW-Kraftfeld, Chem. Ber., 1991, 124, 2499-2521.  [all data]

Hansen, Zhou, et al., 1995
Hansen, K.C.; Zhou, Z.; Yaws, C.L.; Aminabhavi, T.M., A laboratory method for the determination of Henry's law constants of volatile organic chemicals, J. Chem. Educ., 1995, 72, 93-96.  [all data]

Hansen, Zhou, et al., 1993
Hansen, K.C.; Zhou, Z.; Yaws, C.L.; Aminabhavi, T.M., Determination of Henry's law constants of organics in dilute aqueous solutions, J. Chem. Eng. Data, 1993, 38, 546-550.  [all data]

Yaws and Yang, 1992
Yaws, C.L.; Yang, H.-C., Henry's law constant for compound in water in Thermodynamic and Physical Property Data, C. L. Yaws, ed(s)., Gulf Publishing Company, Houston, TX, 1992, 181-206.  [all data]

Mackay and Shiu, 1981
Mackay, D.; Shiu, W.Y., A critical review of Henry's law constants for chemicals of environmental interest, J. Phys. Chem. Ref. Data, 1981, 10, 1175-1199.  [all data]

Hine and Mookerjee, 1975
Hine, J.; Mookerjee, P.K., The intrinsic hydrophilic character of organic compounds. Correlations in terms of structural contributions, J. Org. Chem., 1975, 40, 292-298.  [all data]

Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P., Ionization energies of homologous organic compounds and correlation with molecular size, Org. Mass Spectrom., 1991, 26, 537.  [all data]

Sieck and Mautner(Meot-Ner), 1982
Sieck, L.W.; Mautner(Meot-Ner), M., Ionization energies and entropies of cycloalkanes. Kinetics of free energy controlled charge-transfer reactions, J. Phys. Chem., 1982, 86, 3646.  [all data]

Lias, 1982
Lias, S.G., Thermochemical information from ion-molecule rate constants, Ion Cyclotron Reson. Spectrom. 1982, 1982, 409.  [all data]

Mautner(Meot-Ner), Sieck, et al., 1981
Mautner(Meot-Ner), M.; Sieck, L.W.; Ausloos, P., Ionization of normal alkanes: Enthalpy, entropy, structural, and isotope effects, J. Am. Chem. Soc., 1981, 103, 5342.  [all data]

Rang, Paldoia, et al., 1974
Rang, S.; Paldoia, P.; Talvari, A., Ionization potentials of unsaturated hydrocarbons. 2. Mono-substituted cyclopentenes and cyclohexenes, Eesti. NSV Tead. Akad. Toim., 1974, 354.  [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369.  [all data]

Pottie, Harrison, et al., 1961
Pottie, R.F.; Harrison, A.G.; Lossing, F.P., Free radicals by mass spectrometry. XXIV. Ionization potentials of cycloalkyl free radicals and cycloalkanes, J. Am. Chem. Soc., 1961, 83, 3204.  [all data]

Notes / Error Report

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Gas Phase IR Spectrum, Mass Spectrum, References

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