Comparison of carbon-silicon hyperconjugation at the 2-and 4-positions of the N-methylpyridinium cation

被引：20

作者：

Hassall, K ^{[1
]}

Lobachevsky, S ^{[1
]}

White, JM ^{[1
]}

机构：

[1] Univ Melbourne, Sch Chem, Parkville, Vic 3010, Australia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 06期

关键词：

D O I：

10.1021/jo048384p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] N-Methyl-2-trialkylsilylmethylpyridinium cations 6a-c and 4-trialkylsilylmethylpyridinium cations 5a-c were prepared and investigated using Si-29 and C-13 NMR and single-crystal X-ray crystallography. Systematic differences in the Si-29 Chemical shifts and Si-29-C-13 one-bond coupling constants for these cations suggested that the Si-CH2 bond interacts more strongly at the 2-position of the electron-deficient pyridinium ring than at the 4-position. This result is supported by the X-ray structures of the pyridinium cations 5b and 6b.

引用

页码：1993 / 1997

页数：5

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