In this work, we describe a simple and efficient route for the synthesis of novel N1-substituted benzimidazole derivatives (8-14) by a rearrangement reaction of N1-alkyl-1,5-benzodiazepine-2-thiones (1-7) in the presence of hydroxylamine hydrochloride in boiling ethanol. Good to excellent yields were achieved for a wide range of alkyl partners with both short-chain and long-chain substituents. The title products were identified using 1 H and 13 C-NMR spectroscopic measurements and confirmed by single-crystal X-ray diffraction techniques for 8-10. In addition, we performed theoretical studies of 8-10 using Hirshfeld surface analysis, molecular docking studies and, along with experimental data. The predicted spectral data were obtained using density functional theory (DFT) at the B3LYP/6-311++G(d,p) level of theory. Also, according to Monte Carlo simulations, the inhibition trend is 10 > 8 > 9 toward all metals in an acidic environment. Good inhibition performance is predicted for iron as compared to copper and aluminum metals.

A novel benzodiazepine derivative was prepared and characterized by elemental analysis, FT-IR, NMR ( 1 H and 13 C) and HR-MS methods. Its crystal structure was also investigated by single crystal X-ray diffraction. In the title compound, the fused 6-and 7-membered rings adopt chair and "twist boat" conformations, respectively. In the crystal, the molecules form inversion dimers through N-H⋅⋅⋅O hydrogen bonds and pack with no unusually short intermolecular contacts, which is in agreement with the results of the Hirshfeld surface analysis.The Hirshfeld surface analysis showed that the H⋅⋅⋅H contact was the most important interaction for the studied compound. Based on the DFTÀ B3LYP study, the studied compound owned a little different geometry in the gas phase concerning the solid phase. The molecular docking was performed between the title compound and a mu-opioid receptor. Molecular dynamics studies were also carried up to 50 ns to understand the stability for the title compound complex with the mu-opioid receptor.[a] Dr.

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