N,N'-bis(2-bromobenzylidene)-2,2'-diaminodiphenyldisulfide (BBDD): Insights of crystal structure, DFT, QTAIM, PASS, ADMET and molecular docking studies

• Published in: Journal of molecular structure 2022-11, Vol.1268, p.133657, Article 133657
• Main Authors: Jayashankar, J., Hema, M.K., Mahmoudi, Ghodrat, Masoudiasl, Ardavan, Dušek, Michal, Montazerozohori, Morteza, Karthik, C.S., Lokanath, N.K.
• Format: Article
• Language: English
• Subjects: ADMET; DFT; Disulfide; Hirshfeld surface; Molecular docking
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2022.133657

•Single crystal structure of N,N'-bis(2-bromobenzylidene)-2,2′-diaminodiphenyldisulfide determined by using SC-XRD technique.•The DFT studies, MEP, Hirshfeld surface, Energy framework and QTAIM analysis were done.•Intermolecular contacts and Interaction of BBDD are quantified using Hirshfeld and QTAIM analysis.•Further, ADMET and PASS analysis have been performed for BBDD compound.•The molecular docking of compound (BBDD) with glycosyltransferace protein of S. aureus (PDB ID: 3HZS) is performed. In the present research work, a single crystal of N, N'-bis(2-bromobenzylidene)-2,2′-diaminodiphenyl disulfide (BBDD) is analyzed by S-XRD and computational technique. The crystal structure of BBDD is greatly stabilized by strong C—H⋯Br, C—H⋯S, and C—H⋯H intermolecular hydrogen bond interactions. DFT computation is used to obtain a better understanding of molecular properties. Hirshfeld surfaces analysis and 2D fingerprint plots were used to investigate the unique supramolecular topology produced by diverse intra and intermolecular interactions. The crystal structure was optimized using B3LYP/6-311++G(d, p) basis set and the energy difference between HOMO and LUMO is 3.69 eV indicating the possibility of charge transfer in the BBDD compound. Molecular electrostatic potential (MEP) was plotted to understand the charge distribution. In addition, the 3D topology of the molecular packing is visualized through energy frameworks, reduced density gradient (RDG) analyses are obtained from the quantum theory of atoms in molecules (QTAIM) framework. PASS analysis of compound BBDD has been performed to analyze Pa and Pi values. ADME and toxicity of the compound was also predicted by using pkCSM online tool. Further, molecular docking study of title compound (BBDD) with glycosyltransferace protein (PDB ID:3HZS) of S. aureus which showed good binding score (-7.7 kcal/mol). [Display omitted]