Theoretical gas-phase stabilities of α-trimethylsilyl-substituted tertiary carbenium ions

被引：5
|
作者：
Grunenberg, J
Laschat, S
Dickner, T
机构：
[1] Tech Univ Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany
[2] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 24期
关键词：
silanes; carbenoids; density functional calculations; gas-phase calculations; compliance constants;
D O I：
10.1002/ejoc.200300273
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Theoretical hydride ion affinities in the gas phase are presented for alpha-SiMe3-substituted tertiary carbenium ions. Thermodynamic stabilization of the "nascent" ions by a single trimethylsilyl group is weaker than by a tert-butyl group but comparable to the effect of a methyl group. In the case of the cyclopropenylium cation, the stabilization by a trimethylsilyl group even exceeds the effectiveness of a tertbutyl group. Compliance constants are used to quantify the chemical concept of hyperconjugation. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
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页码：4897 / 4901
页数：5
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