Quantum chemical and X-ray diffraction studies of (E)-3-(((3,4-dimethoxybenzyl)imino)methyl)benzene-1,2-diol

In this study, the target compound, (E)-3-(((3,4-dimethoxybenzyl)imino)methyl)benzene-1,2-diol, has been synthesized and characterized by FT-IR, UV–Vis and 1H NMR, 13C NMR methods. It’s molecular structure has been experimentally elucidated by single crystal X–ray diffraction method. As a result of the X–ray diffraction experiment, it was found that the title molecule is in zwitterionic form. The minimum energy conformation in the gas phase of the title compound was achieved by density functional theory (DFT) method with the B3LYP hybrid functional using 6–31G(d,p) basis set. Accordingly, global (HOMO, LUMO, hardness and softness parameters) and local (MEP, FF, net charges) chemical activity descriptors were investigated. The stability of the molecule arising from hyperconjugative interactions, charge delocalization were analyzed by using natural bond orbital analysis (NBO) and nonlinear optical properties were investigated. Also, the interactions between the molecule with DNA bases such as adenine, cytosine, guanine, and thymine were investigated by using the ECT (electrophilicity-based charge transfer) method and ΔN (charge transfer) for investigating the charge transfer, electrophilic and nucleophilic nature. •The title molecule was efficiently synthesized and optimized by density functional theory (DFT) with B3LYP level of 6–31G(d,p) basis set.•Chemical activity, Fukui functions analysis of the compound were studied.•HS analysis revealed the fingerprint plots and molecular surface contours.•The charge transfer is investigated by using DNA/ECT method.