Synthesis, structural analysis, and antimicrobial properties of (E)-2-((4-fluorobenzylidene) amino) phenol: A combined experimental and computational study

Abstract

Synthetic organic chemistry plays a pivotal role in developing various active compounds with significant therapeutic potential, including Schiff base and its derivatives, which are renowned for their excellent biological properties. This research investigates the synthesis of (E)-2-((4-fluorobenzylidene)amino)phenol (4F2AM) and detailed characterization using various instrumental analyses such as Fourier-transform infrared (FTIR), nuclear magnetic resonance (NMR), ultraviolet–visible (UV–vis), fluorescence spectroscopy, and cyclic voltammetry. The antimicrobial efficiency (antibacterial and antifungal) of the synthesized 4F2AM compound is evaluated both in experimental and computation techniques. A brief density functional theory (DFT) analysis has been performed to understand the structural and physicochemical properties, to validate the ¹H and ¹³C NMR chemical shifts, absorption spectra, NBO, FMO analysis, thermodynamic characteristics, and dipole moments, a brief density functional theory (DFT) analysis has been performed to understand the structural and physicochemical properties of the synthesized 4F2AM compound. Computational results demonstrate exceptional concordance with experimental data, such as FTIR, ¹H and ¹³C NMR and UV-vi absorption analysis. The synthesized 4F2AM compound showed significant antibacterial efficacy, against the gram-positive (S. aureus), gram-negative (E. coli), and fungus (C. albicans). The antibacterial properties of the 4F2AM compounds are further investigated through molecular docking and molecular dynamics simulations, to understand their biochemical interactions. This study highlights the potential of the synthesized 4F2AM compound that may be applied in biological fields.