Bicyclo[4.2.0]octa-1,3,5-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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Δvap43.7 ± 0.1kJ/molVRoth, Biermann, et al., 1978ALS
Δvap43.7kJ/molN/ARoth, Biermann, et al., 1978DRB

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
323.6 to 324.0.027Buckingham and Donaghy, 1982BS

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-54.8kJ/molKinRoth and Scholz, 1981gas phase
Δr-44.2 ± 1.9kJ/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-41.2 ± 0.54kJ/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-210.5 ± 0.1kJ/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
Δr46.4 ± 0.8kJ/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

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.

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]

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

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]

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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