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Study on the synthesis and theoretical calculation of a chlorine‐substituted thiosemicarbazone derivative
Author(s) -
Wei Chenli,
Wang Sifan,
Deng Jingwen,
Guo Zeyu,
Qi Fan,
Huang Jie
Publication year - 2021
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.4211
Subject(s) - chemistry , orthorhombic crystal system , homo/lumo , crystallography , molecule , molecular orbital , hydrogen bond , crystal structure , density functional theory , crystal (programming language) , computational chemistry , intermolecular force , stereochemistry , organic chemistry , computer science , programming language
Abstract In this paper, the compound ( E )‐ N ‐(3,5‐dimethylphenyl)‐2‐(3‐chlorobenzylidene)thiosemicarb‐azone was synthesized and characterized by elemental analysis, Fourier transform infrared (FT‐IR), 1 H nuclear magnetic resonance (NMR), 13 C NMR. The crystal structure was determined by single‐crystal X‐ray diffraction tool, indicating that the compound belongs to the orthorhombic crystal system of the Fdd 2 space group, where a = 14.0472(12) Å, b = 57.148(4) Å, c = 7.9633(6) Å, the chemical formula is C 16 H 16 ClN 3 S, M r = 317.83, V = 6392.7(9) Å 3 , Z = 16, D c = 1.321 Mg/m 3 , F(000) = 2656, R = 0.0339, wR = 0.0903. Analysis of crystal data shows that the molecular conformation has good planarity. Hirshfeld surface and two‐dimensional (2D) fingerprints were used to analyze the intermolecular hydrogen bonds. In addition, a more comprehensive theoretical calculation studies were carried out on synthetic compound, such as potential energy surface (PES) scan, reduced density gradient (RDG), and independent gradient model (IGM) analysis, atoms in molecules (AIM) analysis, highest occupied molecular orbital–lowest unoccupied molecular orbital (HOMO–LUMO) and UV‐visible spectra analysis. The combination of experimental and theoretical data proved that non‐covalent bonds play a vital role in maintaining the stability of molecule. Finally, molecular docking was used to research the interaction between the synthetic compound and the receptor protein (4C2L). Meanwhile, the results obtained by in vitro antifungal assay indicated that the synthetic compound possesses the most remarkable inhibitory effect for Fusarium graminearum .