Cyclohexene, 4-ethenyl-
- Formula: C8H12
- Molecular weight: 108.1809
- IUPAC Standard InChIKey: BBDKZWKEPDTENS-UHFFFAOYSA-N
- 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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Gas phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, References, Notes
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 16.62 ± 0.35 | kcal/mol | Ccb | Kozina, Timofeeva, et al., 1972 | ALS |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
34.085 | 298.15 | Lenz T.G., 1990 | These values calculated by molecular mechanics method are in good agreement with estimation by a group additivity approach [ Dorofeeva O.V., 1997].; GT |
34.285 | 300. | ||
44.577 | 400. | ||
53.791 | 500. | ||
61.926 | 600. | ||
68.987 | 700. | ||
74.969 | 800. | ||
79.873 | 900. | ||
83.702 | 1000. |
Phase change data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References, Notes
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 399.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 402.2 | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 403.2 | K | N/A | Lebedev and Skawronskaja, 1911 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 9.467 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 9.15 | kcal/mol | V | Rauh, Geyer, et al., 1973 | ALS |
ΔvapH° | 9.51 | kcal/mol | N/A | Kozina, Timofeeva, et al., 1972 | DRB |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.01 | 402.2 | N/A | Majer and Svoboda, 1985 | |
9.58 | 307. | A | Stephenson and Malanowski, 1987 | Based on data from 292. to 405. K.; AC |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change data, References, Notes
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
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.8 ± 0.1 | EI | Groenwold and Gross, 1984 | LBLHLM |
8.93 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C4H6+ | 10.9 ± 0.1 | C4H6 | EI | Groenwold and Gross, 1984 | LBLHLM |
C6H7+ | 9.5 ± 0.1 | C2H5 | EI | Groenwold and Gross, 1984 | LBLHLM |
C7H9+ | 9.8 ± 0.1 | CH3 | EI | Groenwold and Gross, 1984 | LBLHLM |
References
Go To: Top, Gas phase thermochemistry data, Phase change 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.
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
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- 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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