Experimental and theoretical investigation of the unusual substituent effect of the vinyl group

σ + Substituent constants for the ortho- and para-vinyl group have been determined by the application of the linear free-energy relationship to the nitration of the β-substituted styrene derivatives.Energy changes (relative to benzene system) for the proton and hydride ion transfer to individual pos...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 58; no. 4; pp. 412 - 417
Main Authors Reynolds, W. F, Modro, T. A, Mezey, P. G, Skorupowa, E, Maron, A
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 15.02.1980
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Summary:σ + Substituent constants for the ortho- and para-vinyl group have been determined by the application of the linear free-energy relationship to the nitration of the β-substituted styrene derivatives.Energy changes (relative to benzene system) for the proton and hydride ion transfer to individual positions in the styrene molecule have been calculated. Both approaches indicate that the vinyl group is capable of stabilizing both positively and negatively charged transition states. The interactions of the vinyl group with other substituents in the phenyl ring are also determined. Again, stabilizing effects with respect to both π-donor and π-acceptor substituents have been demonstrated for the vinyl group.
ISSN:0008-4042
1480-3291
DOI:10.1139/v80-066