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13C NMR spectral assignment of 1,4-diarylpiperazinones

✍ Scribed by Arturo Abreu; Ma. Eugenia Ochoa; Norberto Farfán; Rosa Santillan

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
118 KB
Volume
44
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The piperazinone derivatives have potential application in the pharmaceutical, polymer and textile fields. The present work describes the preparation of a series of new 1,4‐diarylsubstituted‐2‐piperazinones by condensation of substituted N,N′‐bis‐(2‐hydroxyphenyl)‐ethylenediamines with glyoxal and the complete ^13^C NMR spectral assignment accomplished using APT, HMQC and HMBC techniques. Substituent chemical‐shift effects (SCS) were calculated, which showed different values for the lactam‐ and amine‐substituted aromatic rings. The results show that predictions based on SCS effects are not simple for these molecules due to electronic and steric effects. Moreover, in the case of the ortho‐substituted derivative 2 g, the NMR spectra reveal a dynamic behavior related to restricted rotation of the phenyl groups (atropisomerism). Copyright © 2005 John Wiley & Sons, Ltd.

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