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

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

doi:10.1002/anie.200501633

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

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

Research output: Contribution to journal › Article › peer-review

48 Citations (Scopus)

Abstract

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).

Original language	English
Pages (from-to)	823-826
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	5
DOIs	https://doi.org/10.1002/anie.200501633
Publication status	Published - 23 Jan 2006
Externally published	Yes

Keywords

α-stabilization
Bond theory
Carbanions
Density functional calculations
Substituent effects

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200501633

Cite this

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title = "α-Stabilization of carbanions: Fluorine is more effective than the heavier halogens",

abstract = "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).",

keywords = "α-stabilization, Bond theory, Carbanions, Density functional calculations, Substituent effects",

author = "Bickelhaupt, \{F. Matthias\} and Hermann, \{Holger L.\} and Gernot Boche",

year = "2006",

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T1 - α-Stabilization of carbanions

T2 - Fluorine is more effective than the heavier halogens

AU - Bickelhaupt, F. Matthias

AU - Hermann, Holger L.

AU - Boche, Gernot

PY - 2006/1/23

Y1 - 2006/1/23

N2 - 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).

AB - 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).

KW - α-stabilization

KW - Bond theory

KW - Carbanions

KW - Density functional calculations

KW - Substituent effects

UR - https://www.scopus.com/pages/publications/31444445628

U2 - 10.1002/anie.200501633

DO - 10.1002/anie.200501633

M3 - Article

AN - SCOPUS:31444445628

SN - 1433-7851

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 5

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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