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

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 P2(1)/c space group with unit cell parameters a = 14.2897 (13) angstrom, b = 5.4068 (4) angstrom, c = 16.2386 (14) angstrom, V = 1242.81 (18) angstrom(3) and Z = 4. The molecular packing is stabilized by N/C-H center dot center dot center dot Br and N-H center dot center dot center dot Se hydrogen bonds, Br center dot center dot center dot Br interactions, C-H center dot center dot center dot pi, 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 center dot center dot center dot H (38%), C center dot center dot center dot H (27.7%), Br center dot center dot center dot H (17.7%) and Se center dot center dot center dot 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. [GRAPHICS] .

Automated summary

A novel organoselenium compound was synthesized and its crystal structure and intermolecular interactions were studied using X-ray diffraction. The experimental results showed that the compound has a significant contribution from dispersion energy and its molecular charge distribution was visualized.