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Stereoelectronic Properties, Stereospecificity and Stabilization of α‐Seleno Carbanions. An ab initio Study
Author(s) -
Lehn JeanMarie,
Wipff Georges,
Demuynck Jean
Publication year - 1977
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19770600413
Subject(s) - carbanion , chemistry , ab initio , sulfur , stereospecificity , lone pair , computational chemistry , atomic orbital , stereochemistry , organic chemistry , catalysis , molecule , quantum mechanics , physics , electron
An ab initio study of α‐seleno carbanions show that they are subject to appreciable polarization and stereoelectronic effects. Like in α‐thia carbanions, the equatorial e forms are more stable than the axial a forms, one of the stabilizing contributions being the conformation dependent (C‐lone pair, σ* SeZ) interaction. The carbanion stabilizing effect of the α‐Se atom is about 3 kcal/mol larger than that of the sulfur analog. As in the case of the sulfur no specific effect of the d orbitals is found.