Title

Conformational and Configurational Analysis of an N,N Carbonyl Dipyrrinone-Derived Oximate and Nitrone by NMR and Quantum Chemical Calculations

Document Type

Article

Publication Date

5-1-2011

Department

Chemistry and Biochemistry

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 H-1/C-13 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 (C) 2011 John Wiley & Sons, Ltd.

Publication Title

Magnetic Resonance in Chemistry

Volume

49

Issue

5

First Page

205

Last Page

212