Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthesis of Asymmetric Pyrazoline Derivatives from Phenylthiophenechalcones; DFT Mechanistic Study

  • Aboelnaga, Asmaa (Department of Chemistry, Faculty of Women for Arts, Science and Education, Egypt, Ain Shams University) ;
  • Mansour, Eman (Department of Chemistry, Faculty of Women for Arts, Science and Education, Egypt, Ain Shams University) ;
  • Ahmed, Hoda. A. (Faculty of Science, Department of Chemistry, Cairo University) ;
  • Hagar, Mohamed (Faculty of Science, Chemistry Department, Alexandria University)
  • Received : 2020.12.21
  • Accepted : 2021.01.18
  • Published : 2021.04.20
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Abstract

New phenylthiophenechalcones,1-(biphenyl-4-yl)-3-(5-phenylthiophen-2-yl)prop-2-en-1-one (3a) and 3-(5-phenylthiophen-2-yl)-1-(4-(piperidin-1-yl) phenyl) prop-2-en-1-one (3b) were synthesized, next, their treatment with thiosemicarbazide in ethanol afforded their pyrazoline derivatives (4a) and (4b), respectively. The molecular structures of the synthesized compounds were confirmed via elemental analysis, FT-IR, 1H, 13C NMR and mass spectroscopy. The geometrical elucidation of four suggested conformers has been studied for these compounds. DFT calculations have been performed to study the stability and the structural parameters of the predicted conformers and revealed that orientation of the biphenyl and the phenylthiophene moieties affect the stability of the estimated conformers of the synthesized chalcones and pyrazoline. Moreover, two reaction mechanisms have been proposed to illustrate the reaction products and the DFT calculations have been used to confirm the reaction mechanism of the pyrazoline compounds.

Keywords

References

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