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

Jean‐Marie Lehn; Georges Wipff; Jean Demuynck

doi:10.1002/hlca.19770600413

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

Jean‐Marie Lehn
, Georges Wipff
, Jean Demuynck

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

74 Citations (Scopus)

Abstract

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* SeZ) 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. Copyright © 1977 Verlag GmbH & Co. KGaA, Weinheim

Original language	English
Pages (from-to)	1239-1246
Journal	Helvetica Chimica Acta
Volume	60
Issue number	4
DOIs	https://doi.org/10.1002/hlca.19770600413
Publication status	Published - 1 Jun 1977
Externally published	Yes

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Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

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title = "Stereoelectronic Properties, Stereospecificity and Stabilization of α‐Seleno Carbanions. An ab initio Study",

abstract = "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* SeZ) 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. Copyright {\textcopyright} 1977 Verlag GmbH \& Co. KGaA, Weinheim",

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AU - Lehn, Jean‐Marie

AU - Wipff, Georges

AU - Demuynck, Jean

N1 - Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

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N2 - 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* SeZ) 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. Copyright © 1977 Verlag GmbH & Co. KGaA, Weinheim

AB - 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* SeZ) 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. Copyright © 1977 Verlag GmbH & Co. KGaA, Weinheim

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DO - 10.1002/hlca.19770600413

M3 - RGC 21 - Publication in refereed journal

SN - 0018-019X

VL - 60

SP - 1239

EP - 1246

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

IS - 4

ER -

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

Abstract

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