Synthesis, Spectroscopic, Computational and Biological Investigations of Substituted 2-((Phenylimino)methyl)phenol

The Schiff bases (E)-4-bromo-2-((phenylimino)methyl)phenol [I], (E)-4-bromo-2-(((2-methoxyphenyl)imino)methyl)phenol [II] and (E)-4-bromo-2-(((5-chloro-2-methylphenyl)imino)methyl)phenol [III] were synthesized and characterized by elemental analysis, infrared, ultraviolet, proton and carbon-13 nuclear magnetic resonance. The computational investigations were done via Density Functional Theory calculations which were performed on the modelled and optimized structures of the compounds through Becke’s three-parameter hybrid functional employing the Lee-Yang-Parr correlation functional and the Empirical Density Functional 1 methods with 6-31G** basis set. The infrared, ultraviolet, proton and carbon-13 nuclear magnetic resonance spectra of the compounds were calculated and the results compared with the corresponding experimental spectra to enhance the structural elucidation. The experimental and calculated results were in good agreement. The biological investigations revealed that the compounds displayed antibacterial and antioxidant activities