Ambident reactivity of the nitrite ion revisited

被引：46
|
作者：
Tishkov, AA
Schmidhammer, U
Roth, S
Riedle, E
Mayr, H
机构：
[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
[2] Univ Munich, Lehrstuhl Biomol Opt, D-80538 Munich, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 29期
关键词：
HSAB principle; kinetics; Klopman-Salem equation; Kornblum's rule; nitro compounds;
D O I：
10.1002/anie.200501274
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Lost control: The rationalization of the ambident reactivity of NO2- by the change between charge control to orbital control has to be revised. SN1-type reactions of carbocations with NO2- give kinetically controlled product mixtures only when these reactions proceed without activation energy (diffusion control). Activation-controlled SN1 alkylations are reversible and lead to the thermodynamically more stable nitro compounds. © 2005 Wiley-VCH Verlag GmbH &Co. KGaA.
引用
收藏
页码：4623 / 4626
页数：4
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