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Structures, stabilities, and energies of isomerization of α‐cyano and α‐isocyano carbanions
Author(s) -
Moffat J. B.
Publication year - 1982
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560220209
Subject(s) - carbanion , isomerization , chemistry , delocalized electron , computational chemistry , ab initio , stereochemistry , organic chemistry , catalysis
Ab initio STO ‐3 G calculations show that α‐cyano‐ and α‐isocyano‐substitution on carbanions produce a significant approximately equal stabilization of these charged species. Evidence is presented which suggests that the mechanism of such stabilization is qualitatively different for the cyano and isocyano substituents. The former appears to act through an electron delocalization process while the latter may operate by an inductive effect.