Crystal structure analysis of (E)‐N‐(3,5‐dimethylphenyl)‐2‐(substituted benzylidene)thiosemicarbazone: Experimental and theoretical studies,Journal of Physical Organic Chemistry

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Crystal structure analysis of (E)‐N‐(3,5‐dimethylphenyl)‐2‐(substituted benzylidene)thiosemicarbazone: Experimental and theoretical studies
Journal of Physical Organic Chemistry ( IF 1.9 ) Pub Date : 2020-09-21 , DOI: 10.1002/poc.4138
Sifan Wang ₁ , Xing Zhang ₁ , Fan Qi ₁ , Jie Huang ₁ , Chenli Wei ₁ , Zeyu Guo ₁

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Two novel thiosemicarbazone derivatives (E)‐N‐(3,5‐dimethylphenyl)‐2‐(3‐methylbenzylidene)thiosemicar‐bazone (1) and (E)‐N‐(3,5‐dimethylphenyl)‐2‐(3‐fluorobenzylidene)thiosemicarbazone (2) had been synthesized and characterized by FT‐IR, nuclear magnetic resonance, and elemental analysis. Single crystal X‐ray diffraction analysis showed that compound 1 belongs to triclinic system in P‐1 space group and compound 2 belongs to monoclinic system in C2/c space group. It could be seen from the determined crystal structure that the central skeleton NNHC(S)NH of both thiosemicarbazone compounds have good planarity. Density functional theory (DFT) calculations were done using B3LYP/6‐31+G(d, p) basis set and the calculated results are in good agreement with the experimental data. In addition, the UV‐visible absorption spectrum was estimated based on TD‐DFT quantum chemistry calculations. Likewise, the simulated absorption spectrum is very consistent with the experimental data. Combining Hirshfeld surface analysis and molecular structure, it was found that the intermolecular hydrogen bond NH···SC constitutes central symmetric dimer $urn:x-wiley:08943230:media:poc4138:poc4138-math-0001$ . Through quantum chemical calculation, we investigated the reduced density gradient function and the independent gradient model, which provided a deeper insight into the intermolecular and intramolecular interaction force of the compounds. The frontier molecular orbital analysis and molecular electrostatic potential were also discussed by theoretical calculations.

中文翻译：

（E）-N-（3,5-二甲基苯基）-2-（取代的亚苄基）硫代半脲的晶体结构分析：实验和理论研究

两种新的硫代半碳酰胺衍生物（E）‐ N‐（3,5-二甲基苯基）‐2‐（3‐甲基亚苄基）硫半碳ba（1）和（E）‐N‐（3,5-‐二甲基苯基）‐2‐（3合成了-氟亚苄基）硫代半碳酰胺（2）并通过FT-IR，核磁共振和元素分析对其进行了表征。X射线单晶衍射分析表明，化合物1在P-1空间群中属于三斜晶系，化合物2在C2 / c空间群中属于单斜晶系。它可以从所确定的晶体结构，所述中心骨架N可以看出 NH  C（S） NH两种硫半脲化合物的均具有良好的平面度。密度泛函理论（DFT）使用B3LYP / 6‐31 + G（d，p）基集进行计算，计算结果与实验数据吻合良好。此外，根据TD-DFT量子化学计算估算了紫外线可见吸收光谱。同样，模拟的吸收光谱与实验数据非常一致。组合Hirshfeld表面分析和分子结构，可知分子间氢键Ñ  ħ···SC构成中心对称二聚体 $骨灰盒：x-wiley：08943230：media：poc4138：poc4138-math-0001$ 。通过量子化学计算，我们研究了降低的密度梯度函数和独立的梯度模型，从而更深入地了解了化合物的分子间和分子内相互作用力。理论计算也讨论了前沿的分子轨道分析和分子静电势。

更新日期：2020-09-21

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