Investigating the Structural and in-Silico Bioactive Properties of a Newly Synthesized Schiff Base Compound through Experimental and Computational Approaches

Abstract

A new Schiff base compound, (E)–2–[(2–bromophenylimino)methyl]–4,6–dichloro–3–methoxyphenol, was obtained from the condensation reaction of 3,5–dichloro–2–hydroxy–6–methoxybenzaldehyde and 2–bromoaniline in ethanol. Single-crystal XRD studies revealed that the planarity in 3D molecular structure with 5.2° between the two aromatic rings and the crystal packing pattern which is formed by weak intermolecular C―H···O hydrogen bonds and π···π interactions. Geometry optimizations with Gaussian and Slater-type basis sets revealed the molecule's planarity to be significantly distorted at 40.2°. Fingerprint plots and energy frameworks were generated using the Hirshfeld surface analysis approach to better comprehend crystal packing and show the quantity of intermolecular interaction energies. To confirm the suitability of the chosen computational methods, root mean square errors in bond lengths and angles were calculated for the two calculated structures and the experimental structure. Intramolecular charge transfer effects on the molecule have been investigated with the scan and NBO calculations using Gaussian-type basis sets, which were time-saving basis sets in the geometry optimizations. Using experimental FT–IR/UV spectra and calculated ones, molecular electronic configuration outlined in solid-state and solvent media. Molecular docking studies were carried out to examine the compound's potential inhibitory activities against hMAOB protein, and binding energy was found as -8.84 kcal/mol.