A Dual Methodology Comprising Experimental and Theoretical Techniques to Study the Synthesis, Characterization, and Supramolecular Assembly of Schiff Bases Derived from Benzocaine

Benzocaine is known for its antibacterial, anticancer, antitumor, and antifungal properties. Herein, a series of three new Schiff bases is synthesized by reacting benzocaine with salicylaldehyde (E4AS), 2,3-dihydroxybenzaldehyde (E4ADH), and 5-chlorosalicylaldehyde (E4ACl). These benzocaine-based Schiff bases were characterized by a variety of spectroscopic methods, including FTIR, NMR, (1H and 13C), and elemental analysis (CHN). Additionally, the single crystal X-ray diffraction method was used to reveal the molecular structures of the derivatives. Solid-state X-ray crystal structures of E4AS and E4ACl adopted enol tautomeric form, whereas keto-tautomeric form was found in E4ADH. The supramolecular assembly of the compounds was probed by Hirshfeld surface analysis. The void analysis was executed to predict the mechanical response of the compounds. Additionally, UV–Vis spectroscopy and molecular docking practices were used to look into the DNA binding abilities of the benzocaine-based Schiff bases. The geometries of the molecules were fully optimized and studied for their electronic structural properties of respective compounds. The frontier molecular orbitals and molecular electrostatic potentials were studied to predict the properties of molecules. The study provides molecular-level intuitions into the synthesis and prospective uses of these Schiff bases in the arena of general and medicinal chemistry.