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α‐Stabilization of Carbanions: Fluorine Is More Effective than the Heavier Halogens

2005; Wiley; Volume: 45; Issue: 5 Linguagem: Inglês

10.1002/anie.200501633

1521-3773

F. Matthias Bickelhaupt, Holger L. Hermann, Gernot Boche,

Chemical Reaction Mechanisms

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 CH2X− 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.