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 Copy

  
• IUPAC Standard InChIKey: VIQRCOQXIHFJND-UHFFFAOYSA-N Copy
• 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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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
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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

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

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
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of fusion

Enthalpy of phase transition

Entropy of phase transition

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

=  + 

By formula: C₈H₁₂ = C₆H₈ + C₂H₄

 +  =

By formula: H₂ + C₈H₁₂ = C₈H₁₄

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:
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

IR Spectrum

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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

• gas; HP-GC/MS/IRD

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, 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]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Wong and Westrum, 1970, 2
Wong, W.-K.; Westrum, E.F., 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, 1303-8. [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]

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

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• 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)
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  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
  ΔfusH	Enthalpy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH°	Enthalpy of sublimation at standard conditions

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