Molecular structural, vibrational assignments, electronic structure and DFT calculations, and molecular docking of N-benzylideneaniline and N-salicylidene-o-aminoaphenol Schiff bases

Abstract

Two Schiff bases N-benzylidenaniline (BZA) and N-salicylidene-o-aminoaphenol (SAP) were synthesized. Structure of SAP was determined by Xrd analysis. It was found that SAP crystallized with two molecules perpendicular to each other and connected by inter- and intramolecular hydrogen bonding. The compound crystallized in the triclinic space group P-1 with a Z value of 2. Geometry optimization of BZA and SAP were investigated by DFT (Gaussian 09W) and REDF2 (Spartan 14). The optimized structure of SAP is consistent with that obtained from the Xrd analysis. Quantum global reactivity descriptors of the two compounds were calculated using the HOMO and LUMO energy values. IR, Raman and theoretical calculations (DFT method) of the vibrational modes of the two derivatives in the wavenumber range 1700–200 cm−1 using Gaussian 09W and Spartan 14 software were carried out. Molecular docking of the two reported compounds with either B-DNA (1ZEW) or protein (4MZI) were studied.