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Exocyclic Charge Flight from Cyclopropenide Systems as a Criterion of Antiaromaticity
Author(s) -
Mitchell R. David,
Bauld Nathan L.
Publication year - 1980
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198000091
Subject(s) - mindo , antiaromaticity , chemistry , charge (physics) , computational chemistry , ion , moiety , homo/lumo , perturbation (astronomy) , wave function , stereochemistry , chemical physics , atomic physics , organic chemistry , quantum mechanics , molecule , aromaticity , physics
The unusually extensive exocyclic charge flight (from cyclopropenyl to organo moiety) proposed for the cyanocyclopropenide ion is affirmed by MINDO/3 calculation. Nevertheless, the MINDO/3 wave function for this ion is shown not to be absolutely antiaromatic. The basis for exocyclic charge flight is shown, using the “de‐perturbation” approach, to be the small (cyclopropenide) HOMO/ (cyano) LUMO gap.