Stereoelectronic Properties, Stereospecificity and Stabilization of α‐Seleno Carbanions. An ab initio Study | Zendy

Lehn JeanMarie | Zendy; Wipff Georges | Zendy; Demuynck Jean | Zendy

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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.

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