Unusual Tautomeric Energetics in 4 n Azaheterocycles

Unusual imino preference in 4n azaheterocycles is theoretically analyzed. It is attributed to less topological charge stability of the amino forms due to antisymmetric nonbonding molecular orbitals. The theory is applicable for designing stable imino species. The same analysis is also applicable for...

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Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 2015-08, Vol.88 (8), p.1147-1149
Main Author: Hatanaka, Masashi
Format: Article
Language:English
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Summary:Unusual imino preference in 4n azaheterocycles is theoretically analyzed. It is attributed to less topological charge stability of the amino forms due to antisymmetric nonbonding molecular orbitals. The theory is applicable for designing stable imino species. The same analysis is also applicable for hydroxyl/oxo tautomerism, and results in very stable lactams.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20150105