Synthesis, spectroscopic characterization and in-silico bio-activity studies of (E)-4,6-dibromo-2-[(2-bromo-4-methylphenylimino)methyl]-3-methoxyphenol

Abstract

(E)-4,6-dibromo-2-[(2-bromo-4-methylphenylimino)methyl]-3-methoxyphenol was synthesized for the first time and it was characterized by experimental and computational methods. Molecular structure, intra and intermolecular interactions were obtained from single crystal X-ray diffraction studies. Aromatic rings of the titled molecule lie nearly in one plane and C−H•••Br hydrogen bonds and π•••π stacking interactions play important roles in crystal stabilizing and packing. Experimental FT-IR spectrum bands were assigned to the normal coordinates by using computational Potential Energy Distribution analysis. Experimental and calculated UV-Vis. spectra of the compound in ethanol (polar-protic), DMSO (polar-aprotic) and chloroform (apolar) solvents were analysed to obtain information about the keto-enol tautomeric equilibrium. 1H and 13C interpretations of the compound were done with the help of the calculated spectra. Natural Orbital Fukui Functions, which are Natural Bond Orbital based chemical reactivity descriptors, were defined to obtain chemically favourable sites. in-silico ADMET and α-glucosidase docking studies were carried out to get estimations about the biological activity of the compound. Computational NLO analysis shows that polarizability of the compound was 9 times and the hyperpolarizability was 14 times higher than urea.