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α‐Stabilization of Carbanions: Fluorine Is More Effective than the Heavier Halogens
Author(s) -
Bickelhaupt F. Matthias,
Hermann Holger L.,
Boche Gernot
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200501633
Subject(s) - carbanion , halogen , chemistry , fluorine , contradiction , medicinal chemistry , organic chemistry , philosophy , epistemology , alkyl
Ready steady go! The basicity of the carbanions CH 2 X − 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 CH 2 X − : F stabilizes CH 2 X − more effectively than Cl, Br, and I (see picture). This apparent contradiction results from the usually ignored stabilization of the corresponding acids CH 3 X by X.