Synthesis, single crystal X-ray, Hirshfeld surface analysis and DFT calculation based NBO, HOMO-LUMO, MEP, ECT and molecular docking analysis of N'-[(2,6-dichlorophenyl)methylidene]-2-{[3-(trifluoromethyl)phenyl]amino}benzohydrazide

A. Suhta, S. Saral, U. Çoruh, S. Karakuş, E.M. Vazquez-Lopez
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Abstract

A new Schiff base compound of N'-[(2,6-dichlorophenyl)methylidene]-2-{[3-(trifluoromethyl)phenyl]amino}benzohydrazide was synthesized and characterized through various spectroscopic techniques, including infrared, 1H NMR, 13C NMR spectroscopy and X–ray diffraction. Experimental results collected by XRD were compared with theoretical results obtained from Density functional theory method. Hirshfeld surface analysis was used to obtain three dimension molecular surface and two dimension fingerprint plots to illustrate the intermolecular bonding. Theoretical calculations provide valuable insights into both global and local chemical activity, as well as the properties of molecules and chemicals, including their nucleophilic and electrophilic nature. The DFT method at B3LYP/6–311++G (d,p) basis set was employed to study the optimized structure and geometric parameters, as well as to explore the frontier molecular orbitals, global reactive parameters, Mullikan population analaysis, Natural bond orbital and molecular electrostatic potential characteristics which cannot be obtained by experimental methods. Additionally, electrophilicity based charge transfer study was carried out with DNA bases to determine the direction of charge transfer. Finally, an investigation was carried out using molecular docking analysis to examine the binding energies of the title compound with PDB ID: 2QDJ protein target. The analysis yielded significant insights into the possible interactions, offering valuable findings in the process.
N'-[(2,6-dichlorophenyl)methylidene]-2-{[3-(trifluoromethyl)phenyl]amino}benzohydrazide 的合成、单晶 X 射线、Hirshfeld 表面分析和基于 NBO、HOMO-LUMO、MEP、ECT 的 DFT 计算及分子对接分析
合成了一种新的 N'-[(2,6-二氯苯基)亚甲基]-2-{[3-(三氟甲基)苯基]氨基}苯甲酰肼希夫碱化合物,并通过各种光谱技术(包括红外光谱、1H NMR 光谱、13C NMR 光谱和 X 射线衍射)对其进行了表征。X 射线衍射的实验结果与密度泛函理论的理论结果进行了比较。利用 Hirshfeld 表面分析法获得了三维分子表面和二维指纹图,以说明分子间的键合情况。理论计算为了解全局和局部化学活性以及分子和化学物质的性质(包括亲核性和亲电性)提供了宝贵的见解。我们采用 B3LYP/6-311++G (d,p) 基集的 DFT 方法研究了优化结构和几何参数,并探索了实验方法无法获得的前沿分子轨道、全局反应参数、Mullikan 种群分析、自然键轨道和分子静电势特征。此外,还对 DNA 碱基进行了基于亲电性的电荷转移研究,以确定电荷转移的方向。最后,研究人员使用分子对接分析方法研究了标题化合物与 PDB ID: 2QDJ 蛋白靶标的结合能。该分析对可能的相互作用产生了重要的见解,并在此过程中提供了有价值的发现。
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