Synthesis and Structure of Polycyclic 1,2,3-Triazolylmethyl-benzimidazole Derivatives — Experimental and Computational Quantum Chemical Studies

Three novel triazolo-benzimidazolyl derivatives have been designed and efficiently synthesized via Cu -catalyzed azide-alkyne cycloaddition (CuAAC) reaction between the N-propargyl benzimidazole and di-verse arylazides. Compounds ( 6a-c ) were characterized by spectroscopic techniques (H-1 and C-13 NMR) and the solid-state structure of derivative 6b was elucidated by X-ray crystallography. The compound crystallizes in the triclinic system with P-1 space group, as single molecule in the asymmetric unit. The supramolecular conformation is stabilized by miscellaneous network of intermolecular interactions, mainly C-H center dot center dot center dot N(O) H-bonds. The nature and energetics of key non-covalent interactions were analysed based on the Hirshfeld surface and further confirmed through Atoms-In-Molecules (AIM) topological technique. Moreover, Mappings of electrostatic potential (MEP) and Parr functions were used for the identification of the probable reactive sites. (C) 2022 Elsevier B.V. All rights reserved.