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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

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Abstract

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 (SN) 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 (Edis = -184.4 kJ/mol) contribution is preponderant over the electrostatic energy (Eele = -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.

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Acknowledgements

The authors extend their appreciation to the Deanship of Scientific Research at Imam Mohammad Ibn Saud Islamic University for funding this work through Research Group no. RG-21-09-68.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, King Faisal University, P.O. Box 380, Al-Ahsa, 31982, Saudi Arabia

    Saad Shaaban

  2. Organic Chemistry Division, Department of Chemistry, College of Science, Mansoura University, Mansoura, Egypt

    Saad Shaaban & Marwa Abdel-Motaal

  3. Department of Chemistry, College of Science, Imam Mohammad Ibn Saud Islamic University (IMSIU), Riyadh, 11623, Saudi Arabia

    Hela Ferjani & Tarek Yousef

  4. Toxic and Narcotic Drug, Forensic Medicine Department, Mansoura Laboratory, Medicolegal Organization, Ministry of Justice, Mansoura, Egypt

    Tarek Yousef

  5. Department of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi Arabia

    Marwa Abdel-Motaal

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  1. Saad Shaaban
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Contributions

All authors contributed to the study conception and design. Material preparation, data collection and analysis were performed by SS, HF, TY and MAM. The first draft of the manuscript was written by SS, HF and TY and all authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

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Correspondence to Hela Ferjani.

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Shaaban, S., Ferjani, H., Yousef, T. et al. 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. J Inorg Organomet Polym 32, 1878–1890 (2022). https://doi.org/10.1007/s10904-022-02284-2

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