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Conformational and configurational analysis of an N , N carbonyl dipyrrinone‐derived oximate and nitrone by NMR and quantum chemical calculations
Author(s) -
Walton Ian,
Davis Marauo,
Yang Liu,
Zhang Yong,
Tillman Destin,
Jarrett William L.,
Huggins Michael T.,
Wallace Karl J.
Publication year - 2011
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2728
Subject(s) - chemistry , nitrone , quantum chemical , carbon 13 nmr , computational chemistry , chemical shift , stereochemistry , organic chemistry , molecule , cycloaddition , catalysis
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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