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
IUPAC Standard InChIKey: RHCCUQVVABYRDN-UHFFFAOYSA-N
CAS Registry Number: 500-24-3
Chemical structure:
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Information on this page:
Other data available:
- Phase change data
- Reaction thermochemistry data
Data at other public NIST sites:
- Gas Phase Kinetics Database
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Gas phase ion energetics data

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
8.23	PE	Haselbach, Heilbronner, et al., 1971	LLK
8.24	PE	Bodor, Dewar, et al., 1970	RDSH
7.95 ± 0.10	EI	Franklin and Carroll, 1969	RDSH
8.23	PE	Gleiter, Bohm, et al., 1983	Vertical value; LBLHLM

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₃H₃⁺	13.64 ± 0.25	?	EI	Franklin and Carroll, 1969	RDSH
C₄H₂⁺	17.20 ± 0.30	2C₂H₂+H₂	EI	Franklin and Carroll, 1969	RDSH
C₄H₃⁺	18.04 ± 0.10	2C₂H₂+H	EI	Franklin and Carroll, 1969	RDSH
C₄H₄⁺	15.31 ± 0.20	2C₂H₂	EI	Franklin and Carroll, 1969	RDSH
C₅H₃⁺	16.11 ± 0.10	?	EI	Franklin and Carroll, 1969	RDSH
C₆H₅⁺	14.49 ± 0.10	C₂H₂+H	EI	Franklin and Carroll, 1969	RDSH
C₆H₆⁺	10.50 ± 0.10	C₂H₂	EI	Franklin and Carroll, 1969	RDSH
C₈H₆⁺	11.97 ± 0.20	H₂	EI	Franklin and Carroll, 1969	RDSH
C₈H₇⁺	10.63 ± 0.10	H	EI	Franklin and Carroll, 1969	RDSH

References

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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

Go To: Top, Gas phase ion energetics data, References

Symbols used in this document:

AE Appearance energy
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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