Bicyclo[2.2.2]octa-2,5,7-triene

• Formula: C₈H₈
• Molecular weight: 104.1491
• IUPAC Standard InChI: InChI=1S/C8H8/c1-2-8-5-3-7(1)4-6-8/h1-8H Copy

  
• IUPAC Standard InChIKey: RHCCUQVVABYRDN-UHFFFAOYSA-N Copy
• CAS Registry Number: 500-24-3
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Information on this page:
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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 by: William E. Acree, Jr., James S. Chickos

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

3 +  =

By formula: 3H₂ + C₈H₈ = 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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C₈H₈⁺ (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.

Kusano, 1985
Kusano, Kazuhito, Micro conduction calorimeters to measure enthalpies of vaporization, Thermochimica Acta, 1985, 88, 1, 109-120, https://doi.org/10.1016/0040-6031(85)85418-6 . [all data]

Turner, 1964
Turner, R.B., Heat of Hydrogenation of Bicyclo[2.2.2]octa-2,5,7-triene, J. Am. Chem. Soc., 1964, 86, 3586-3587. [all data]

Haselbach, Heilbronner, et al., 1971
Haselbach, E.; Heilbronner, E.; Schroder, G., The interaction of π-orbitals in barrelene, Helv. Chim. Acta, 1971, 54, 153. [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]

Franklin and Carroll, 1969
Franklin, J.L.; Carroll, S.R., The effect of molecular structure on ionic decomposition. I. An electron impact study of seven C₈H₈ isomers, J. Am. Chem. Soc., 1969, 91, 5940. [all data]

Gleiter, Bohm, et al., 1983
Gleiter, R.; Bohm, M.C.; de Meijere, A.; Preuss, T., Electronic structure and reactivity of homobarrelene derivatives, J. Org. Chem., 1983, 48, 796. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH°	Enthalpy of vaporization at standard conditions

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