Get access

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

Authors


  • We thank the Netherlands Organization for Scientific Research (NWO-CW), the Fonds der Chemischen Industrie (FCI), and the Deutsche Forschungsgemeinschaft (DFG), Sonderforschungsbereich 260, for financial support.

Abstract

original image

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 CH2Xmore effectively than Cl, Br, and I (see picture). This apparent contradiction results from the usually ignored stabilization of the corresponding acids CH3X by X.

Get access to the full text of this article

Ancillary