α-Stabilization of carbanions:: Fluorine is more effective than the heavier halogens

被引：47

作者：

Bickelhaupt, FM

Hermann, HL

Boche, G

机构：

[1] Vrije Univ Amsterdam, Afdeling Theoret Chem, Scheikundig Lab, NL-1081 HV Amsterdam, Netherlands

[2] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 05期

关键词：

alpha-stabilization; bond theory; carbanions; density functional calculations; substituent effects;

D O I：

10.1002/anie.200501633

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ready steady go! The basicity of the carbanions CH2X- decreases continuously in the series X=F, Cl, Br, I. However, contrary to the common assumption, this occurs not because of the increasing α-stabilization of CH2X-: F stabilizes CH 2X more effectively than Cl, Br, and I (see picture). This apparent contradiction results from the usually ignored stabilization of the corresponding acids CH3X by X. (Graph Presented). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：823 / 826

页数：4

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