Research Article Open Access

The Investigation of 1H NMR Spectra of 2,3-Dihydro-4-Pyridinones Derived from Bisdemethoxycurcumin

Wisam A. Radhi1 and Bahjat A. Saeed1
  • 1 ,
American Journal of Applied Sciences
Volume 7 No. 8, 2010, 1053-1056

DOI: https://doi.org/10.3844/ajassp.2010.1053.1056

Submitted On: 28 July 2010 Published On: 31 August 2010

How to Cite: Radhi, W. A. & Saeed, B. A. (2010). The Investigation of 1H NMR Spectra of 2,3-Dihydro-4-Pyridinones Derived from Bisdemethoxycurcumin. American Journal of Applied Sciences, 7(8), 1053-1056. https://doi.org/10.3844/ajassp.2010.1053.1056

Abstract

Problem statement: The studied dihydropyridones were synthesized via microwave assisted reaction of bisdemethoxycurcumin and amines or amine acetates which is new approach in the synthesis of this important class of compounds and the deep study of their NMR spectra seems reasonable. Approach: 1H NMR spectra of dihydropyridones derived from curcumin were discussed and their structures were elucidated accordingly. Results: The one dimentional, HOMO-and HETERO-COSY spectra indicated the presence of two doublets of doublets signals of two geminaly coupled protons with 2J values of 16 Hz. Both these protons coupled to the same vicinal proton within a six-membered ring with 3J coupling constants of 3J values of 7 and 4 Hz. Computational calculations using B3LYP/6-311+G(d,p)//B3LYP/6-31G(d,p) level of theory were undertaken to predict the chemical shifts of one molecule via the GIAO method. Conclusion: The above mentioned theoretical method affords good approach for the prediction of the NMR spectra of the studied compounds.

  • 1,170 Views
  • 3,192 Downloads
  • 1 Citations

Download

Keywords

  • Bis-demethoxycurcumin
  • dihydropyridones
  • geminal coupling
  • DFT
  • GIAO method