Cyclohexene, 1-methyl-

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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas-19.42 ± 0.19kcal/molCcbLabbauf and Rossini, 1961 

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δcliquid-1048.85 ± 0.16kcal/molCcbLabbauf and Rossini, 1961Corresponding Δfliquid = -19.40 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δcliquid-1047.3kcal/molCcbZubova, 1901Corresponding Δfliquid = -20.9 kcal/mol (simple calculation by NIST; no Washburn corrections)

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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil382. ± 4.KAVGN/AAverage of 21 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus152.71KN/AStreiff, Schultz, et al., 1957Uncertainty assigned by TRC = 0.04 K; TRC
Tfus152.75KN/AStreiff, Schultz, et al., 1957Uncertainty assigned by TRC = 0.03 K; TRC
Tfus152.700KN/AStreiff, Schultz, et al., 1957Uncertainty assigned by TRC = 0.05 K; TRC
Tfus152.2KN/ABoord, Henne, et al., 1949Uncertainty assigned by TRC = 0.5 K; TRC
Tfus152.15KN/AAnonymous, 1943Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Δvap8.96 ± 0.05kcal/molGSVerevkin, Wandschneider, et al., 2000Based on data from 275. to 313. K.; AC
Δvap9.04kcal/molVCamin and Rossini, 1960ALS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
9.01 ± 0.05294.GSVerevkin, Wandschneider, et al., 2000Based on data from 275. to 313. K.; AC
8.53348.AStephenson and Malanowski, 1987Based on data from 333. to 384. K. See also Eisen and Orav, 1970 and Boublik, Fried, et al., 1984.; AC
8.77324.MMCamin and Rossini, 1960, 2Based on data from 309. to 384. K.; AC

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

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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

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

Cyclohexene, 1-methyl- + Trifluoroacetic acid = Acetic acid, trifluoro-, 1-methyl cyclohexyl ester

By formula: C7H12 + C2HF3O2 = C9H13F3O3

Quantity Value Units Method Reference Comment
Δr-8.74 ± 0.21kcal/molCacWiberg, Wasserman, et al., 1985liquid phase; solvent: Trifluoroacetic acid; Trifluoroacetolysis

Cyclohexene, 1-methyl- + Hydrogen chloride = 1-Chloro-1-methylcyclohexane

By formula: C7H12 + HCl = C7H13Cl

Quantity Value Units Method Reference Comment
Δr-13.41 ± 0.21kcal/molCmArnett and Pienta, 1980liquid phase; solvent: Methylene chloride; Hydrochlorination

Cyclohexane, methylene- = Cyclohexene, 1-methyl-

By formula: C7H12 = C7H12

Quantity Value Units Method Reference Comment
Δr-1.71 ± 0.07kcal/molEqkYursha, Kabo, et al., 1974gas phase; Heat of isomerization at 463 K

Cyclohexene, 3-methyl- = Cyclohexene, 1-methyl-

By formula: C7H12 = C7H12

Quantity Value Units Method Reference Comment
Δr-1.93 ± 0.07kcal/molEqkYursha, Kabo, et al., 1974gas phase; Heat of isomerization at 463 K

Cyclohexene, 4-methyl- = Cyclohexene, 1-methyl-

By formula: C7H12 = C7H12

Quantity Value Units Method Reference Comment
Δr-1.39 ± 0.07kcal/molEqkYursha, Kabo, et al., 1974gas phase; Heat of isomerization at 463 K

References

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

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

Labbauf and Rossini, 1961
Labbauf, A.; Rossini, F.D., Heats of combustion, formation, and hydrogenation of 14 selected cyclomonoolefin hydrocarbons, J. Phys. Chem., 1961, 65, 476-480. [all data]

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

Streiff, Schultz, et al., 1957
Streiff, A.J.; Schultz, L.H.; Hulme, A.R.; Tucker, J.A.; Krouskop, N.C.; Rossini, F.D., Purification, Purity, and Freezing Points of 20 API Standard API Research Hydrocarbons, Anal. Chem., 1957, 29, 361. [all data]

Boord, Henne, et al., 1949
Boord, C.E.; Henne, A.L.; Greenlee, K.W.; Perilstein, W.L.; Derfer, J.M., The Grignard Reagent in hydrocarbon synthesis, Ind. Eng. Chem., 1949, 41, 609. [all data]

Anonymous, 1943
Anonymous, R., , Sunbury Rep. No. 2176, Anglo-Iranian Oil Co., 1943. [all data]

Verevkin, Wandschneider, et al., 2000
Verevkin, Sergey P.; Wandschneider, Dirk; Heintz, Andreas, Determination of Vaporization Enthalpies of Selected Linear and Branched C 7 , C 8 , C 9 , C 11 , and C 12 Monoolefin Hydrocarbons from Transpiration and Correlation Gas-Chromatography Methods, J. Chem. Eng. Data, 2000, 45, 4, 618-625, https://doi.org/10.1021/je990297k . [all data]

Camin and Rossini, 1960
Camin, D.L.; Rossini, F.D., Physical properties of to selected C7 and C8 alkene hydrocarbons, J. Chem. Eng. Data, 1960, 5, 368. [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]

Eisen and Orav, 1970
Eisen, O.; Orav, A., Eesti NSV Tead. Akad. Toim. Keem. Geol., 1970, 19, 3, 202. [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]

Camin and Rossini, 1960, 2
Camin, D.L.; Rossini, F.D., Physical Properties of 16 Selected C 7 and C 8 Alkene Hydrocarbons., J. Chem. Eng. Data, 1960, 5, 3, 368-372, https://doi.org/10.1021/je60007a037 . [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]

Wiberg, Wasserman, et al., 1985
Wiberg, K.B.; Wasserman, D.J.; Martin, E.J.; Murcko, M.A., Enthalpies of hydration of alkenes. 3. Cycloalkenes, J. Am. Chem. Soc., 1985, 107, 6019-6022. [all data]

Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J., Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions, J. Am. Chem. Soc., 1980, 102, 3329-3334. [all data]

Yursha, Kabo, et al., 1974
Yursha, I.A.; Kabo, G.Ya.; Andreevskii, D.N., Equilibriums and thermodynamics of the isomerization of methylcyclohexenes, Neftekhimiya, 1974, 14, 688-693. [all data]


Notes

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