Three-membered ring amides - a calculational and conceptual study of the structure and energetics of 1,2-oxaziridine-3-one and aziridine-2,3-dione

• Type: Article in International Scientific Journal
• Date: 2015

Authors

Margarida S Miranda (Author) Other; Paulo J O Ferreira (Author) Other; Joaquim C G E Esteves da Silva (Author) FCUP; Joel F Liebman (Author) Other

Journal

Title: Canadian Journal of Chemistry

Vol. 93

Pages: 406-413

ISSN: 0008-4042

Publisher: NRC Research Press

Indexing

ISI Web of Knowledge - 5 Citations

Scopus - 5 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-00A-9C3

DOI: 10.1139/cjc-2014-0321

Abstract (EN): Species with three-membered rings and the amide linkage are well studied. A quick perusal of the literature with SciFinder finds some 50 000 references to cyclopropanes and almost 300 000 references to amides. In the current paper, we discuss the structure and energetics of two understudied three-membered ring amides, 1,2-oxaziridine-3-one (5) (simultaneously describable as the simplest cyclic carbamate and simplest hydroxamate) and aziridine-2,3-dione (7) (simultaneously describable as the simplest imide and simplest alpha-ketoamide), with but 5 and nearly 10 references, respectively, for these two classes of compounds. Neither 1,2-oxaziridine-3-one (5) nor aziridine-2,3-dione (7), nor any derivative thereof, has been isolated. Calculational theory ameliorates the paucity of experimental information. The current study reports our computational findings for these and related species (e.g., enols and imidols) where we have used the G3(MP2)//B3LYP method.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 8