NMR SPECTROSCOPIC AND COMPUTATIONAL INVESTIGATIONS OF SIGMA-INTERACTIONS IN CARBOCATIONS - THE BETA-SILYL EFFECT IN VINYL CATIONS

被引：22
|
作者：
SIEHL, HU
机构：
[1] Institute of Organic Chemistry, University of Tubingen
来源：
PURE AND APPLIED CHEMISTRY | 1995年 / 67卷 / 05期
基金：
日本学术振兴会;
关键词：
D O I：
10.1351/pac199567050769
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The para carbon chemical shift in 1-mesityl substituted vinyl cations and the torsional barrier for the methoxy group rotation in 1-p(anisyl)vinyl cations are used to evaluate the magnitude of the silyl effect. The hyperconjugative stabilization by beta-silicon groups and the accompanying geometrical distortions are studied experimentally and computationally in dienyl-cations and 1-cyclopropylvinyl cations. A geminal methyl substituent enhances the interaction of a beta-silyl group with the vacant p-orbital.
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页码：769 / 775
页数：7
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