Supramolecular Self-Assembly Built by Hydrogen, Stacking and Br···Br Interactions in 4-((4-Bromobenzyl)Selanyl)Aniline: Structure, Hirshfeld Surface Analysis, 3D Energy Framework Approach and Global Reactivity Descriptors,Journal of Inorganic and Organometallic Polymers and Materials

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Supramolecular Self-Assembly Built by Hydrogen, Stacking and Br···Br Interactions in 4-((4-Bromobenzyl)Selanyl)Aniline: Structure, Hirshfeld Surface Analysis, 3D Energy Framework Approach and Global Reactivity Descriptors
Journal of Inorganic and Organometallic Polymers and Materials ( IF 3.9 ) Pub Date : 2022-03-16 , DOI: 10.1007/s10904-022-02284-2
Saad Shaaban _{1,

2} , Marwa Abdel-Motaal _{2,

3} , Hela Ferjani ₄ , Tarek Yousef _{4,

5}

Affiliation

A novel organoselenium compound named 4-((4-bromobenzyl)selanyl)aniline, C₁₃H₁₂BrNSe, (A), was synthesized via reduction of 4,4′-(1,2-diselandiyl)dianiline with sodium borohydride (NaBH₄) and subsequent nucleophilic substitution (S_N) reaction with 4-((4-bromobenzyl)selanyl)aniline. The single crystal X-Ray Diffraction result indicates that organoselenide (A) crystallizes in monoclinic P2₁/c space group with unit cell parameters a = 14.2897 (13) Å, b = 5.4068 (4) Å, c = 16.2386 (14) Å, V = 1242.81 (18) Å³ and Z = 4. The molecular packing is stabilized by N/C-H···Br and N–H···Se hydrogen bonds, Br···Br interactions, C–H···π, stacking interactions. Hirshfeld surface analysis allowed for better visualization and easier analysis of intermolecular interaction. The two-dimensional fingerprint revealed that the uppermost contributions to these surfaces come from H···H (38%), C···H (27.7%), Br···H (17.7%) and Se···H (8.1%) interactions. The intermolecular interactions energies in organoselenide (A) were calculated using B3LYP/6-31G(p,d) and B3LYP/6-311G(p,d) energy models. It reveals that the dispersion energy (E_dis = -184.4 kJ/mol) contribution is preponderant over the electrostatic energy (E_ele = -75.9 and 88.4 kJ/mol) contribution. The theoretical calculations were carried out using the DFT method to assess the molecular, frontier molecular orbitals, and global reactivity descriptors. The charge distribution in organoselenide (A) is visualized using molecular electrostatic potential surface.

Graphical Abstract

中文翻译：

4-((4-Bromobenzyl)Selanyl)Aniline 中氢、堆积和 Br···Br 相互作用构建的超分子自组装：结构、Hirshfeld 表面分析、3D 能量框架方法和全局反应性描述符

用硼氢化钠 (NaBH) 还原 4,4'-(1,2-二甲苯二基)二苯胺合成了一种新的有机硒化合物，命名为 4-((4-溴苄基)硒基)苯胺 C ₁₃ H ₁₂ BrNSe, ( A) 。 ₄ ) 和随后与 4-((4-溴苄基)硒基)苯胺的亲核取代 (S _{N ) 反应。}单晶 X 射线衍射结果表明有机硒化物 ( A)在单斜P2 ₁ /c空间群中结晶，晶胞参数a = 14.2897 (13) Å, b = 5.4068 (4) Å, c = 16.2386 (14) Å , V = 1242.81 (18) Å ³和Z = 4. 分子堆积由N/CH ··· Br 和N-H ··· Se 氢键、Br ··· Br 相互作用、C-H ··· π、堆积相互作用稳定。Hirshfeld 表面分析允许更好的可视化和更容易的分子间相互作用分析。二维指纹显示，对这些表面的贡献最大的是H ··· H(38%)、C ··· H(27.7%)、Br ··· H(17.7%)和Se ··· H (8.1%) 互动。使用 B3LYP/6-31G(p,d) 和 B3LYP/6-311G(p,d) 能量模型计算有机硒化物 ( A)中的分子间相互作用能量。它揭示了色散能（E_dis = -184.4 kJ/mol) 贡献比静电能 (E _ele = -75.9 和 88.4 kJ/mol) 贡献占优势。使用 DFT 方法进行理论计算，以评估分子、前沿分子轨道和全局反应性描述符。有机硒化物 ( A)中的电荷分布使用分子静电势表面可视化。

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更新日期：2022-03-16

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