Bicyclo[2.2.2]oct-2-ene
- Formula: C8H12
- Molecular weight: 108.1809
- IUPAC Standard InChI: InChI=1S/C8H12/c1-2-8-5-3-7(1)4-6-8/h1-2,7-8H,3-6H2
- 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, Gas phase ion energetics data, IR Spectrum, 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 | 26. | kJ/mol | Kin | Huybrechts, Rigaux, et al., 1980 | Diels-Alder addition at 560°K, see Van Mele, Boon, et al., 1986; ALS |
| ΔfH°gas | 20.4 ± 0.79 | kJ/mol | Ccr | Wong and Westrum, 1971 | See Westrum and Wong, 1967; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°gas | 316.3 | J/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 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, IR Spectrum, 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
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 |
|---|---|---|---|
| 8.92 | PE | Bodor, Dewar, et al., 1970 | RDSH |
| 9.05 ± 0.02 | PE | Brown and Marcinko, 1978 | Vertical value; LLK |
| 9.03 | PE | Hentrich, Gunkel, et al., 1974 | Vertical value; LLK |
| 9.07 | PE | Asmus and Klessinger, 1974 | Vertical value; LLK |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, References, Notes
Data compiled by: Coblentz Society, Inc.
- GAS (6 TORR VS. EVACUATED CELL) $$ SEE ALSO SPECTRA NO. 10422 AND 10423; CARY 90 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm-1 resolution
- GAS (6 mmHg) VS. EVACUATED CELL; CARY 90 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- SOLUTION (10% WT/VOL IN CCl4 FOR 4000-1570, 10% WT/VOL IN CS2 FOR 1570-450 CM-1) VS. SOLVENT; CARY 90 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- SOLUTION (30% WT/VOL IN CCl4 FOR 4000-1590, 30% WT/VOL IN CS2 FOR 1590-450 CM-1) VS. SOLVENT; CARY 90 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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]
Bodor, Dewar, et al., 1970
Bodor, N.; Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. III. Ionization potentials of some cyclic hydrocarbons and their derivatives, and heats of formation and ionization potentials calculated by the MINDO SCF MO method,
J. Am. Chem. Soc., 1970, 92, 19. [all data]
Brown and Marcinko, 1978
Brown, R.S.; Marcinko, R.W.,
Influence of substituents upon ionization potential. Dependence of the π-ionization energy on the orientation of an allylic hydroxyl or methoxyl substituent,
J. Am. Chem. Soc., 1978, 100, 5721. [all data]
Hentrich, Gunkel, et al., 1974
Hentrich, G.; Gunkel, E.; Klessinger, M.,
Photoelektronenspektren organischer verbindungen. 4. Photoelektronenspektren ungesattigter carbonylverbindungen,
J. Mol. Struct., 1974, 21, 231. [all data]
Asmus and Klessinger, 1974
Asmus, P.; Klessinger, M.,
Photoelectron spectra of organic compounds. VI. Exocyclic methylene compounds,
Tetrahedron, 1974, 30, 2477. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
S°gas Entropy of gas at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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