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


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

Quantity Value Units Method Reference Comment
Deltavap10.3 ± 0.02kcal/molCKusano, 1985 

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

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Individual Reactions

3Hydrogen + Bicyclo[2.2.2]octa-2,5,7-triene = Bicyclo[2.2.2]octane

By formula: 3H2 + C8H8 = C8H14

Quantity Value Units Method Reference Comment
Deltar-93.78 ± 0.31kcal/molChydTurner, 1964liquid phase; solvent: Acetic acid

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

IE (eV) Method Reference Comment
8.23PEHaselbach, Heilbronner, et al., 1971LLK
8.24PEBodor, Dewar, et al., 1970RDSH
7.95 ± 0.10EIFranklin and Carroll, 1969RDSH
8.23PEGleiter, Bohm, et al., 1983Vertical value; LBLHLM

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+13.64 ± 0.25?EIFranklin and Carroll, 1969RDSH
C4H2+17.20 ± 0.302C2H2+H2EIFranklin and Carroll, 1969RDSH
C4H3+18.04 ± 0.102C2H2+HEIFranklin and Carroll, 1969RDSH
C4H4+15.31 ± 0.202C2H2EIFranklin and Carroll, 1969RDSH
C5H3+16.11 ± 0.10?EIFranklin and Carroll, 1969RDSH
C6H5+14.49 ± 0.10C2H2+HEIFranklin and Carroll, 1969RDSH
C6H6+10.50 ± 0.10C2H2EIFranklin and Carroll, 1969RDSH
C8H6+11.97 ± 0.20H2EIFranklin and Carroll, 1969RDSH
C8H7+10.63 ± 0.10HEIFranklin and Carroll, 1969RDSH

References

Go To: Top, Phase change data, Reaction thermochemistry 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.

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 «pi»-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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