Synthesis of Asymmetric Pyrazoline Derivatives from Phenylthiophenechalcones; DFT Mechanistic Study

Journal of the Korean Chemical Society

article

Asmaa Aboelnaga¹  Eman Mansour¹  Hoda A Ahmed²  Mohamed Hagar³ 

[1] Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams University;Faculty of Science, Department of Chemistry, Cairo University;Faculty of Science, Chemistry Department, Alexandria University

关键词: Phenylthiophenechalcone;    Conformers;    Carbothioamide;    Pyrazole;    DFT;    Mechanistic study;   

DOI  :  10.5012/jkcs.2021.65.2.113

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

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, 1 H, 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.

【 授权许可】

Unknown