A New Synthetic Route and Comprehensive Topological Study of a Benzimidazole Derivative

Vitor Duarte,Raquel Naves,Christian Alonso,Hamilton Napolitano,Eduardo Faria,Guilherme Oliveira,Adailton Bortoluzzi,Aline Da Silva

doi:10.21577/0103-5053.20210149

Abstract

Benzimidazole and its derivatives are molecules that have diverse biological properties, therefore we synthesized and studied a new benzimidazole to understand their physical/chemical properties. The compound was obtained through a new synthetic route, using graphite oxide, in the absence of solvent, with crystalline packaging supported by C–H…N and C–H…π interactions. According to the frontier molecular orbitals, the compound is kinetically stable while the molecular electrostatic potential map confirms the site of molecular interactions involving nitrogen atoms and the π-system. This comprehensive study on synthesis, structural description and theoretical calculations can support ongoing studies in pharmaceutical science.

Highlights

Benzimidazole and its derivatives are widely studied due to their biological and clinical application
In this work we describe a new synthetic route for the 1-(2-methoxy-benzyl)2‐(2-methoxy-phenyl)-2,3-dihydro-1H-benzoimidazole (AM2), as well as its structural description, supramolecular arrangement analysis and theoretical calculations, to understand the physical/chemical properties of this compound and support ongoing application work in the pharmaceutical science
The AM2 compound was obtained through a new synthetic route, by using graphite oxide in the absence of solvent, occurring at 80 °C, and within a time interval of 60 min

Summary

Introduction

Benzimidazole and its derivatives are widely studied due to their biological and clinical application. The Hirshfeld surfaces were generated from the X-ray data, representing the frontier between regions where the electron distribution is dominated by the contribution of the interior molecule and the neighboring. These surfaces are bases of the normalized contact distances (de: distance from the surface to the nearest atom in the molecule itself; di: distance from the surface to the nearest atom in another molecule).[27,28,29] In addition, the Hirshfeld analysis allows us to understand the quantitative of the interactions and the empty space in the crystalline structure. Said isosurface contains approximately 98% of the electrical charges of a molecule and determines the volume of the voids.[31,32] Total crystallographic data for AM2 molecule was deposited in the Cambridge Crystallographic Data Centre (CCDC)[33] under the code 2091809

Computational procedures

Results and Discussion

Conclusions