Bicyclo[4.2.0]octa-1,3,5-triene


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

o-Xylylene = Bicyclo[4.2.0]octa-1,3,5-triene

By formula: C8H8 = C8H8

Quantity Value Units Method Reference Comment
Δr-13.1kcal/molKinRoth and Scholz, 1981gas phase
Δr-10.6 ± 0.45kcal/molCmRoth, Biermann, et al., 1978liquid phase

C8H8N2O = Nitrous oxide + Bicyclo[4.2.0]octa-1,3,5-triene

By formula: C8H8N2O = N2O + C8H8

Quantity Value Units Method Reference Comment
Δr-9.85 ± 0.13kcal/molKinOth, Olsen, et al., 1977liquid phase; solvent: THF; At 413 K

3Hydrogen + Bicyclo[4.2.0]octa-1,3,5-triene = Bicyclo[4.2.0]octane

By formula: 3H2 + C8H8 = C8H14

Quantity Value Units Method Reference Comment
Δr-50.32 ± 0.03kcal/molChydTurner, Goebel, et al., 1968liquid phase; solvent: Acetic acid

Bicyclo[4.2.0]octa-1,3,5-triene = o-Xylylene

By formula: C8H8 = C8H8

Quantity Value Units Method Reference Comment
Δr11.1 ± 0.2kcal/molEqkRoth, Ebbrecht, et al., 1988gas phase

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 C8H8+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
8.74 ± 0.05EIFranklin and Carroll, 1969RDSH
8.66 ± 0.03PEHeilbronner, Hoshi, et al., 1976Vertical value; LLK
8.66PEBrogli, Giovannini, et al., 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+14.16 ± 0.15?EIFranklin and Carroll, 1969RDSH
C4H2+17.69 ± 0.302C2H2+H2EIFranklin and Carroll, 1969RDSH
C4H3+18.68 ± 0.102C2H2+HEIFranklin and Carroll, 1969RDSH
C4H4+16.01 ± 0.152C2H2EIFranklin and Carroll, 1969RDSH
C5H3+17.34 ± 0.10C2H2+CH3?EIFranklin and Carroll, 1969RDSH
C6H5+15.58 ± 0.10C2H2+HEIFranklin and Carroll, 1969RDSH
C6H6+11.55 ± 0.10C2H2EIFranklin and Carroll, 1969RDSH
C8H6+11.84 ± 0.10H2EIFranklin and Carroll, 1969RDSH
C8H7+11.94 ± 0.10HEIFranklin and Carroll, 1969RDSH

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.

Roth and Scholz, 1981
Roth, W.R.; Scholz, B.P., Energy profile of the o-quinodimethane = benzocyclobutene equilibrium. Part 2., Chem. Ber., 1981, 114, 3741-3750. [all data]

Roth, Biermann, et al., 1978
Roth, W.R.; Biermann, M.; Dekker, H.; Jochems, R.; Mosselman, C.; Hermann, H., Energy profile of the o-quinodimethane-benzocyclobutene equilibrium, Chem. Ber., 1978, 111, 3892-3903. [all data]

Oth, Olsen, et al., 1977
Oth, J.F.M.; Olsen, H.; Synder, J.P., Energetics of heteroextrusion reactions. N2 vs. N2O, J. Am. Chem. Soc., 1977, 99, 8505-8507. [all data]

Turner, Goebel, et al., 1968
Turner, R.B.; Goebel, P.; Mallon, B.J.; Doering, W.E.; Coburn, J.F., Jr.; Pomerantz, M., Heats of hydrogenation. VIII. Compounds with three- and four-membered rings, J. Am. Chem. Soc., 1968, 90, 4315-4322. [all data]

Roth, Ebbrecht, et al., 1988
Roth, W.R.; Ebbrecht, T.; Beitat, A., o-Quinodimethane-benzocyclobutene equilibrium: oxygen trapping technique, Chem. Ber., 1988, 121, 1357-1358. [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]

Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K., Alkyl-induced, natural hypsochromic shifts of the 2A←2X and 2B←2X transitions of azulene and naphthalene radical cations, Nouv. J. Chim., 1976, 1, 105. [all data]

Brogli, Giovannini, et al., 1973
Brogli, F.; Giovannini, E.; Heilbronner, E.; Schurter, R., Die photoelektronen spektren der benzocycloalkene, Chem. Ber., 1973, 106, 961. [all data]


Notes

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