Cyclohexane, methyl-

• Formula: C₇H₁₄
• Molecular weight: 98.1861
• IUPAC Standard InChI: InChI=1S/C7H14/c1-7-5-3-2-4-6-7/h7H,2-6H2,1H3 Copy

  
• IUPAC Standard InChIKey: UAEPNZWRGJTJPN-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-87-2
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Isotopologues:
  • Methylcyclohexane-d14
• Other names: Cyclohexylmethane; Hexahydrotoluene; Methylcyclohexane; Sextone B; Toluene hexahydride; Hexahydroxytoluene; Metylocykloheksan; Toluene, hexahydro-; UN 2296; NSC 9391
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

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

Constant pressure heat capacity of liquid

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

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (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 compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: 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

 +  =

By formula: C₇H₁₂ + H₂ = C₇H₁₄

 +  =

By formula: H₂ + C₇H₁₂ = C₇H₁₄

2 +  =

By formula: 2H₂ + C₇H₁₀ = C₇H₁₄

Henry's Law 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 by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• GAS (30 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm^-1 resolution
• SOLUTION (10% IN CCl4 FOR 3800-1300, 10% IN CS2 FOR 1300-650, AND 10% IN CCl4 FOR 650-250 CM^-1) VERSUS SOLVENT; PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

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

• gas

Mass spectrum (electron ionization)

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

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law 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.

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]

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]

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]

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

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

Douslin and Huffman, 1946, 2
Douslin, D.R.; Huffman, H.M., The heat capacities, heats of transition, heats of fusion and entropies of cyclopentane, methylcyclopentane and methylcyclohexane., J. Am. Chem. Soc., 1946, 68, 173. [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]

Kudchadker, Alani, et al., 1968
Kudchadker, A.P.; Alani, G.H.; Zwolinski, B.J., The Critical Constants of Organic Substances, Chem. Rev., 1968, 68, 659. [all data]

Kay, 1947
Kay, W.B., Vapor Pressures and Saturated Liquid and Vapor DEensities of Cyclopentane, Methylcyclopentane, Ethylcyclopentane, and Methylcyclohexane, J. Am. Chem. Soc., 1947, 69, 1273-7. [all data]

Simon, 1957
Simon, M., Methods and Apparatus Used at the Bureau of Physicochemical Standards XV. Critical Constants and Straight-Line Diameters of Ten Hydrocarbons, Bull. Soc. Chim. Belg., 1957, 66, 375-81. [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]

Sapei, Uusi-Kyyny, et al., 2010
Sapei, Erlin; Uusi-Kyyny, Petri; Keskinen, Kari I.; Alopaeus, Ville, Phase equilibria of binary systems of 3-methylthiophene with four different hydrocarbons, Fluid Phase Equilibria, 2010, 288, 1-2, 155-160, https://doi.org/10.1016/j.fluid.2009.11.004 . [all data]

Wu, Pividal, et al., 1991
Wu, Huey S.; Pividal, Katherine A.; Sandler, Stanley I., Vapor-liquid equilibria of hydrocarbons and fuel oxygenates, J. Chem. Eng. Data, 1991, 36, 4, 418-421, https://doi.org/10.1021/je00004a021 . [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]

Valerga, 1970
Valerga, Antone J., Entropy and Related Thermodynamic Properties of Tetramethylgermane, J. Chem. Phys., 1970, 52, 9, 4545, https://doi.org/10.1063/1.1673681 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Eubank, Cediel, et al., 1984
Eubank, P.T.; Cediel, L.E.; Holste, J.C.; Hall, K.R., Enthalpies for toluene and methylcyclohexane in the fluid state, J. Chem. Eng. Data, 1984, 29, 389-393. [all data]

Majer, Svoboda, et al., 1979
Majer, Vladimír; Svoboda, Václav; Hála, Slavoj; Pick, Jirí, Temperature dependence of heats of vaporization of saturated hydrocarbons C5-C8; Experimental data and an estimation method, Collect. Czech. Chem. Commun., 1979, 44, 3, 637-651, https://doi.org/10.1135/cccc19790637 . [all data]

Spitzer and Pitzer, 1946
Spitzer, Ralph; Pitzer, Kenneth S., The Heat Capacity of Gaseous Cyclopentane, Cyclohexane and Methylcyclohexane, J. Am. Chem. Soc., 1946, 68, 12, 2537-2538, https://doi.org/10.1021/ja01216a032 . [all data]

Willingham, Taylor, et al., 1945
Willingham, C.B.; Taylor, W.J.; Pignocco, J.M.; Rossini, F.D., Vapor pressures and boiling points of some paraffin, alkylcyclopentane, alkylcyclohexane, and alkylbenzene hydrocarbons, J. RES. NATL. BUR. STAN., 1945, 35, 3, 219-17, https://doi.org/10.6028/jres.035.009 . [all data]

Stuckey and Saylor, 1940
Stuckey, James M.; Saylor, John H., The Vapor Pressures of Some Organic Compounds. I. ¹, J. Am. Chem. Soc., 1940, 62, 11, 2922-2925, https://doi.org/10.1021/ja01868a011 . [all data]

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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]

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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]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  S°gas	Entropy of gas at standard conditions
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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