Conference paper

Bonding in Functionalized Aziridines: Nitrogen-15 and Carbon-13 Studies

P. Tarburton ; Department of Chemistry, University of Nebraska, Lilicoln, Nebraska, USA
J. P. Edasery ; Department of Chemistry, University of Nebraska, Lilicoln, Nebraska, USA
C. A. Kingsbury ; Department of Chemistry, University of Nebraska, Lilicoln, Nebraska, USA
V. W. Day ; Department of Chemistry, University of Nebraska, Lilicoln, Nebraska, USA
C. S. Day ; Department of Chemistry, University of Nebraska, Lilicoln, Nebraska, USA
D. S. Soriano ; Department of Chemistry, University of Nebraska, Lilicoln, Nebraska, USA
K. F. Podraza ; Department of Chemistry, University of Nebraska, Lilicoln, Nebraska, USA
I. Tavaniepour ; Department of Chemistry, University of Nebraska, Lilicoln, Nebraska, USA
N. H. Cromwell ; Department of Chemistry, University of Nebraska, Lilicoln, Nebraska, USA

Abstract

Two isomeric pairs of cis- and trans-1-cyclohexyl-2-phenyl-3-benzoylaziridines
have been synthesized: (1) with a nitrogen-15 labelled nitrogen, and (2) with carbon-13
labelled ring carbons. The carbon-13 to X (where X=nitrogen-15, carbon-13 or
hydrogen-I) spin-spin coupling constants were measured and interpreted in terms
of stereoelectronic effects. X-ray crystallographic data (earlier determined for cisand
trans-1-cyclohexyl-2-phenyl-3-(p-toluyl)aziridines)1 appear in good agreement
with the NMR data. Bonding is discussed for the three-ring itself (NMR studies)
and for its substituents (X-ray studies). It is concluded that stereochemical interaction
of the Van der Waals type is an important determinant of aziridine bond
length. Three-ring to carbonyl hyperconjugation is correlated with stereoelectronic
interactions in the trans isomer.

Keywords

Hrčak ID:

194488

URI

https://hrcak.srce.hr/194488

Publication date:

25.1.1981.

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