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An INDO study of the isomerization of aziridinone
Author(s) -
Talaty Erach R.,
Zandler Melvin E.
Publication year - 1975
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570120127
Subject(s) - chemistry , isomerization , alkyl , nitrogen atom , atom (system on chip) , double bond , dipole , stereochemistry , oxygen atom , computational chemistry , crystallography , catalysis , organic chemistry , molecule , computer science , embedded system
The only pathway postulated in the literature for the isomerization of aziridinone (Ia) to iminooxirane (IIIa) involves a planar, open‐chain, dipolar intermediate (IIa); however, INDO calculations suggest a possible alternative pathway in which an in‐plane bending of the oxygen atom towards the alkyl carbon atom occurs rather than a stretching of the alkyl‐nitrogen bond. INDO calculations also suggest that the unknown compound IIIa has the same degree of stability as Ia.