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

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

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

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 1H/13C 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.

Original languageEnglish
Pages (from-to)205-212
Number of pages8
JournalMagnetic Resonance in Chemistry
Volume49
Issue number5
DOIs
StatePublished - May 2011

Keywords

  • DFT calculations
  • NMR
  • configurational isomers
  • nitrone
  • oxime
  • spin-spin coupling constants

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