Bicyclo[2.2.2]oct-2-ene
- Formula: C8H12
- Molecular weight: 108.1809
- IUPAC Standard InChIKey: VIQRCOQXIHFJND-UHFFFAOYSA-N
- CAS Registry Number: 931-64-6
- 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: Bicyclo[2.2.2]octene; Cyclohexene, 3,6-endo-(1,2-ethanediyl)-; 3,6-Endoethylenecyclohexene; 2,2,2-Bicyclooctene-2; Bicyclo[2.2.2]-2-octene; Bicyclo[2,2,2]-2-octene
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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 | 6.3 | kcal/mol | Kin | Huybrechts, Rigaux, et al., 1980 | Diels-Alder addition at 560°K, see Van Mele, Boon, et al., 1986; ALS |
ΔfH°gas | 4.88 ± 0.19 | kcal/mol | Ccr | Wong and Westrum, 1971 | See Westrum and Wong, 1967; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 75.60 | cal/mol*K | N/A | Cocks A.T., 1971 | This value was calculated from experimental values of entropy for solid bicyclo[2.2.2]oct-2-ene and enthalpy of vaporization. Value of 323.0 J/mol*K was obtained from the study of kinetics of the addition of ethylene to 1,3-cyclohexadiene [ Huybrechts G., 1980]. Estimations by means of the group additivity are equal to 331.0 [ Huybrechts G., 1980] and 330.1 J/mol*K [ Van Mele B., 1986].; GT |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -5.6 ± 0.16 | kcal/mol | Ccr | Wong and Westrum, 1971 | See Westrum and Wong, 1967; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1156.72 ± 0.16 | kcal/mol | Ccr | Wong and Westrum, 1971 | See Westrum and Wong, 1967; Corresponding ΔfHºsolid = -5.58 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 50.301 | cal/mol*K | N/A | Wong and Westrum, 1970 | crystaline, I phase; DH |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
37.459 | 298.15 | Wong and Westrum, 1970 | crystaline, I phase; T = 5 to 500 K.; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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 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: C8H12 = C6H8 + C2H4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 32.4 | kcal/mol | Kin | Huybrechts, Rigaux, et al., 1980 | gas phase; Diels-Alder addition at 560°K, see Van Mele, Boon, et al., 1986 |
By formula: H2 + C8H12 = C8H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -28.25 ± 0.20 | kcal/mol | Chyd | Turner, Meador, et al., 1957 | liquid phase; solvent: Acetic acid |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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.
Huybrechts, Rigaux, et al., 1980
Huybrechts, G.; Rigaux, D.; Vankeerberghen, J.; Van Mele, B.,
Kinetics of the Diels-Alder addition of ethene to cyclohexa-1,3-diene and its reverse reaction in the gas phase,
Int. J. Chem. Kinet., 1980, 12, 253-259. [all data]
Van Mele, Boon, et al., 1986
Van Mele, B.; Boon, G.; Huybrechts, G.,
Gas-phase kinetic and thermochemical data for endo- and exo-5-monosubstituted bicyclo[2.2.2]oct-2-enes,
Int. J. Chem. Kinet., 1986, 18, 537-545. [all data]
Wong and Westrum, 1971
Wong, S.S.; Westrum, E.F., Jr.,
Enthalpies of formation of globular molecules. II. Three bicyclooctanes and two bicyclononanes,
J. Am. Chem. Soc., 1971, 93, 5317-5321. [all data]
Westrum and Wong, 1967
Westrum, E.F., Jr.; Wong, S.,
Strain energies and thermal properties of globular and polynuclear aromatic molecules,
AEC Rept. Coo-1149-92, Contract AT(11-1)-1149, 1967, 1-7. [all data]
Cocks A.T., 1971
Cocks A.T.,
Thermal unimolecular decomposition of bicyclo[2.2.2]oct-2-ene,
J. Chem. Soc. A, 1971, 1661-1663. [all data]
Huybrechts G., 1980
Huybrechts G.,
Kinetics of the Diels-Alder addition of ethene to cyclohexa-1,3-diene and its reverse reaction in the gas phase,
Int. J. Chem. Kinet., 1980, 12, 253-259. [all data]
Van Mele B., 1986
Van Mele B.,
Gas-phase kinetic and thermodynamic data for endo- and exo-5-mono-substituted bicyclo[2.2.2]oct-2-enes,
Int. J. Chem. Kinet., 1986, 18, 537-545. [all data]
Wong and Westrum, 1970
Wong, W-K.; Westrum, E.F., Jr.,
Thermodynamics of globular molecules. XVII. Heat capacities and transition behavior of bicyclo[2.2.2]octane and bicyclo[2.2.2]octene,
J. Phys. Chem., 1970, 74, 1303-1308. [all data]
Turner, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Winkler, R.E.,
Heats of hydrogenation. I. Apparatus and the heats of hydrogenation of bicyclo[2,2,1]heptene, bicyclo[2,2,1]heptadiene, bicyclo[2,2,2]octene and bicyclo[2,2,2]octadiene,
J. Am. Chem. Soc., 1957, 79, 4116-4121. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°gas Entropy of gas at standard conditions S°solid,1 bar Entropy of solid at standard conditions (1 bar) ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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