Synthesis, Physicochemical Characterization, and Biocidal Evaluation of Three Novel Aminobenzoic Acid-Derived Schiff Bases Featuring Intramolecular Hydrogen Bonding.

ABSTRACT: Metal-free aminobenzoic acid-derived Schiff bases are attractive antimicrobial leads because their azomethine (-C=N-) functionality enables tunable electronic properties and target engagement. We investigated whether halogenation on the phenolic ring would modulate the redox behavior and enhance antibacterial potency, and hypothesized that heavier halogens would favorably tune physicochemical and electronic descriptors. We synthesized three derivatives (SB-3/Cl, SB-4/Br, and SB-5/I) and confirmed their structures using FTIR, ¹H- and ¹³C-NMR, UV-Vis, and HRMS. For SB-5, single-crystal X-ray diffraction and Hirshfeld analysis verified the intramolecular O-H⋯N hydrogen bond and key packing contacts. Cyclic voltammetry revealed an irreversible oxidation (aminobenzoic ring

SUBMITTER: Carreno A 

PROVIDER: S-EPMC12608797 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature