Solid-state Zwitterionic Tautomerization of 2-((5-methyl-1H-pyrazol-3-yl)methyl)-1H-benzimidazole: Synthesis, Characterization, DFT Calculation and Docking Studies

Abstract The synthesis, characterization and single crystal X-Ray diffraction structure of 2-((5-methyl-1H-pyrazol-3-yl)methyl)-1H-benzimidazole are reported. The physicochemical characterization of the title compound was performed by spectroscopic techniques like FTIR, NMR analysis and single crystal X-ray diffraction. These data, together with the computed vibrational frequencies and NMR chemical shifts at the B3LYP/6-311++G(d,p) level of theory, are in agreement, and the confirmation of the coexistence of the two Zwitterionic tautomer's in the solid-state is proven using X-ray diffraction. The electronic and structural properties were investigated by DFT method at the geometry-optimized B3LYP/6-311++G(d,p) level. The HOMO-LUMO interactions were also studied. In order to explore the biological importance of the compound, molecular docking interactions have been studied to investigate the inhibition properties of the 2-((5-methyl-1H-pyrazol-3-yl)methyl)-1H-benzoimidazole molecule, indicative of the drug likeliness behavior of the synthesized molecule.