Relative energies of substituted benzene valence isomers |
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Authors: | Arthur Greenberg Joel F. Liebman |
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Affiliation: | Department of Chemical Engineering and Chemistry, New Jersey Institute of Technology, Newark, NJ 07102, U.S.A.;Department of Chemistry, University of Maryland Baltimore County, Catonsville, MD 21228, U.S.A. |
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Abstract: | Ab initio calculations employing the STO-3G basis set are used to obtain the relative energies of the benzene valence isomers and some selected monosubstituted derivatives. We find that 3,3'-bicyclopropenyl, the least stable of the five (CH)6 examined, is slightly more stable in the anti conformation than the gauche (Φ = 45°) conformation in agreement with experiment. Substituents are calculated to produce significant changes in the relative energies of the benzene valence isomers. The ground-state isomerization of 1-Dewar benzeneearbinyl cation to benzyl cation is more exothermic than the aromatization of Dewar benzene, but is, in contrast to the latter, symmetry-allowed. |
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