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

Bickelhaupt F. Matthias | Zendy; Hermann Holger L. | Zendy; Boche Gernot | Zendy

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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.

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