Synthesis, characterization, and in silico studies of 2-[(E)-(2,5-dimethoxybenzylidene)amino]phenol and 3-[(E)-(2,5-dimethoxybenzylidene)amino]phenol

The compounds 2-[( E )-(2,5-dimethoxybenzylidene )amino]phenol (DM2A) and 3-[(E)-(2,5-dimethoxy-benzylidene)amino]phenol (DM3A) were synthesized using a water-methanol mixture at room temper-ature by stirring 2,5-dimethoxybenzaldehyde with 2-aminophenol and 3-aminophenol respectively. The products were characterized using FT-IR, NMR, U.V., and mass spectrometry while molecular structures were determined by X-ray crystallographic analysis of suitable single crystals of the compounds. The X-ray analyses show that the compounds crystallized in a monoclinic crystal system with a space group of (C)2/(c) and Z = 8 for DM2A and a space group of (P)21/(n) and Z = 4 in DM3A unit cells. The presence of vibrational bands around 1591 and 1577 cm -1 characteristic of the azomethine functionality reveals the Schiff base nature of the compounds. The molecular aggregation showed the presence of a number of non-covalent interactions in the two structures. Hirshfeld surfaces analysis was used to investigate the strength of intermolecular interactions in the two compounds. DM2A and DM3A showed strong binding affinities with six different drug targets that are crucial in the development of antidiabetic, antimicrobial, antimalarial, and anticancer drugs.(c) 2022 Elsevier B.V. All rights reserved.