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Conformational and configurational analysis of an N,N carbonyl dipyrrinone-derived oximate and nitrone by NMR and quantum chemical calculations

✍ Scribed by Ian Walton; Marauo Davis; Liu Yang; Yong Zhang; Destin Tillman; William L. Jarrett; Michael T. Huggins; Karl J. Wallace

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 301 KB
Volume: 49
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.2728

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✦ Synopsis

Abstract

The geometries and relative energies of new N,N carbonyl dipyrrinone‐derived oxime molecules (E/Z‐s‐cis 4a and E/Z‐s‐cis 4b) have been investigated. The calculated energies, molecular geometries, and ^1^H/^13^C NMR chemical shifts agree with experimental data, and the results are presented herein. The E‐s‐cis conformations of 4a and 4b and the Z‐s‐cis conformation of 5b were found to be the thermodynamically most stable isomers with the oxime hydrogen atom or the methyl functional group adopting an anti‐orientation with respect to the dipyrrinone group. This conformation was unambiguously supported by a number of 2D NMR experiments. Copyright © 2011 John Wiley & Sons, Ltd.

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## Abstract The ^1^H, ^13^C and ^15^N NMR studies have shown that the __E__ and __Z__ isomers of pyrrole‐2‐carbaldehyde oxime adopt preferable conformation with the __syn__ orientation of the oxime group with respect to the pyrrole ring. The __syn__ conformation of __E__ and __Z__ isomers of pyrrol