Cyclohexane, methyl-

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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
Δfliquid-45.45 ± 0.25kcal/molCcbProsen, Johnson, et al., 1946ALS
Δfliquid-46.67 ± 0.46kcal/molCcbMoore, Renquist, et al., 1940Reanalyzed by Cox and Pilcher, 1970, Original value = -46.02 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Δcliquid-1091.13 ± 0.23kcal/molCcbProsen, Johnson, et al., 1946Corresponding Δfliquid = -45.43 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-1090.89 ± 0.45kcal/molCcbMoore, Renquist, et al., 1940Reanalyzed by Cox and Pilcher, 1970, Original value = -1090.42 ± 0.45 kcal/mol; Corresponding Δfliquid = -45.67 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-1100.6kcal/molCcbZubova, 1901Corresponding Δfliquid = -36.0 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid59.250cal/mol*KN/ADouslin and Huffman, 1946DH
liquid59.30cal/mol*KN/AParks and Huffman, 1930Extrapolation below 90 K, 54.73 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
44.068298.15Shiohama, Ogawa, et al., 1988DH
44.207298.15Tanaka, 1985DH
44.285298.15Grolier, Inglese, et al., 1982T = 298.15 K.; DH
44.17298.15Wilhelm, Grolier, et al., 1979DH
44.178298.15Holzhauer and Ziegler, 1975T = 144 to 312 K. Cp = 129.88277 - 0.0054107773T + 7.9975642x10-4T2 J/mol*K.; DH
44.281298.055Hwa and Ziegler, 1966T = 175 to 308 K. Unsmoothed experimental datum.; DH
44.099298.15Douslin and Huffman, 1946T = 12 to 300 K.; DH
43.50294.2Parks and Huffman, 1930T = 93 to 294 K. Value is unsmoothed experimental datum.; DH

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

Cyclohexane, methylene- + Hydrogen = Cyclohexane, methyl-

By formula: C7H12 + H2 = C7H14

Quantity Value Units Method Reference Comment
Δr-28.56 ± 0.16kcal/molChydRogers, Crooks, et al., 1987liquid phase
Δr-27.75 ± 0.13kcal/molChydTurner and Garner, 1958liquid phase; solvent: Acetic acid
Δr-27.75 ± 0.13kcal/molEqkTurner and Garner, 1957liquid phase; solvent: Acetic acid
Δr-28.70 ± 0.07kcal/molChydTurner and Garner, 1957, 2liquid phase; solvent: Acetic acid

Hydrogen + Cyclohexene, 1-methyl- = Cyclohexane, methyl-

By formula: H2 + C7H12 = C7H14

Quantity Value Units Method Reference Comment
Δr-26.63 ± 0.088kcal/molChydRogers, Crooks, et al., 1987liquid phase
Δr-25.41 ± 0.11kcal/molChydTurner and Garner, 1958liquid phase; solvent: Acetic acid
Δr-25.41 ± 0.11kcal/molChydTurner and Garner, 1957liquid phase; solvent: Acetic acid

2Hydrogen + trans-Bicyclo[4.1.0]hept-3-ene = Cyclohexane, methyl-

By formula: 2H2 + C7H10 = C7H14

Quantity Value Units Method Reference Comment
Δr-92.4 ± 0.1kcal/molChydRoth, Adamczak, et al., 1991liquid phase

Gas phase ion energetics 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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
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

Quantity Value Units Method Reference Comment
IE (evaluated)9.64 ± 0.10eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
9.62 ± 0.05EIHolmes and Lossing, 1991LL
9.64EQSieck and Mautner(Meot-Ner), 1982LBLHLM
9.64 ± 0.10EVALLias, 1982LBLHLM
9.69 ± 0.15EQMautner(Meot-Ner), Sieck, et al., 1981LLK
9.76 ± 0.03PERang, Paldoia, et al., 1974LLK
9.85 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H11+10.95CH3EIPottie, Harrison, et al., 1961RDSH

References

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

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]

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]

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

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