A initio study of the SN2 and E2 mechanisms in the reaction between the cyanide ion and ethyl chloride in dimethyl sulfoxide solution

被引：30

作者：

Almerindo, GI ^{[1
]}

Pliego, JR ^{[1
]}

机构：

[1] Univ Fed Santa Catarina, Dept Quim, BR-88040900 Florianopolis, SC, Brazil

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 09期

关键词：

D O I：

10.1021/ol0504547

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reliable theoretical calculations predict a free energy barrier for nitrile formation from the reaction between the cyanide ion and ethyl chloride in DMSO solvent of 24.1 kcal/mol, close to the experimental value of 22.6 kcal/mol. We have also predicted that the isonitrile formation is less favorable by 4.7 kcal/mol, while the elimination mechanism is less favorable by more than 10 kcal/mol. These results indicate that isonitrile formation and bimolecular elimination are not significant side reactions for primary alkyl chloride reactions.

引用

页码：1821 / 1823

页数：3

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