Cyclohexene, 4-ethenyl-

• Formula: C₈H₁₂
• Molecular weight: 108.1809
• IUPAC Standard InChI: InChI=1S/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2 Copy

  
• IUPAC Standard InChIKey: BBDKZWKEPDTENS-UHFFFAOYSA-N Copy
• CAS Registry Number: 100-40-3
• 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.
• Other names: Cyclohexene, 4-vinyl-; 1-Vinyl-3-cyclohexene; 4-Vinyl-1-cyclohexene; 4-Vinylcyclohexene; 4-Ethenylcyclohexene; Vinylcyclohexene; Butadiene dimer; Cyclohexenylethylene; 4-Ethenyl-1-cyclohexene; 1,2,3,4-Tetrahydrostyrene; 1-Vinylcyclohexene-3; 4-Vinylcyclohexene-1; NCI-C54999; 1-Cyclohexene, 4-vinyl-; 1-Vinylcyclohex-3-ene; NSC 15760
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

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
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

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 compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₈H₁₂⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

References

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

Kozina, Timofeeva, et al., 1972
Kozina, M.P.; Timofeeva, L.P.; Pimenova, S.M.; Aleshina, V.A.; Belikova, N.A.; Bobyleva, A.A.; Plate, A.F., Enthalpies of combustion and of formation of 4-vinylcyclohexene and of certain bicyclic compounds, Russ. J. Phys. Chem. (Engl. Transl.), 1972, 46, 1689-1690. [all data]

Lenz T.G., 1990
Lenz T.G., Force field calculation of equilibrium thermodynamic properties: Diels-Alder reaction of 1,3-butadiene and ethylene and Diels-Alder dimerization of 1,3-butadiene, J. Comput. Chem., 1990, 11, 351-360. [all data]

Dorofeeva O.V., 1997
Dorofeeva O.V., Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 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]

Lebedev and Skawronskaja, 1911
Lebedev, S.; Skawronskaja, F., Zh. Russ. Fiz.-Khim. O-va., Chast Khim., 1911, 43, 1136. [all data]

Rauh, Geyer, et al., 1973
Rauh, H.J.; Geyer, W.; Schmidt, H.; Geiseler, G., Bildungsenthalpien und mesomerieenergien von π-bindungssystemen, Z. Phys. Chem. (Leipzig), 1973, 253, 43-48. [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]

Groenwold and Gross, 1984
Groenwold, G.S.; Gross, M.L., Cation radical diels-alder reaction of 1,3-butadiene: A two-step cycloaddition, J. Am. Chem. Soc., 1984, 106, 6569. [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]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Tboil	Boiling point
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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