Synthesis and structure of polycyclic 1,2,3-triazolylmethyl-benzimidazole derivatives — Experimental and computational quantum chemical studies

Abstract

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 diverse arylazides. Compounds (6a-c) were characterized by spectroscopic techniques (1H and 13C 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…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.