Synthesis and analysis (thermodynamic, electronic, NLO, FMO, NBO, MEP, IR, UV, NMR properties, Hirshfeld surface analysis and molecular docking) of the new Schiff base molecule: (Z)-4‑bromo-2-(((2,4-dimethoxypheny)limino)methyl)-5-fluorophenol

Abstract

A new Schiff-base (Z)-4‑bromo-2-(((2,4-dimethoxyphenyl)imino)methyl)-5-fluorophenol (BDMF) was synthesized and characterized by single-crystal X-ray diffraction, spectroscopic (UV, FT-IR, and NMR), and DFT techniques. Based on DFT computational analysis, Molecular Electrostatic Potential (MESP) 3D plots were used to identify the electrophilic and nucleophilic sites. Based on HOMO-LUMO energies, charge transfer takes place within the molecule, and quantum chemical characteristics were precisely assessed. Additionally, DFT was used to examine charges, molecular orbital contributions, natural bond orbital (NBO), frontier molecular orbital (FMO), nonlinear optic (NLO) analysis, and thermodynamic parameters including enthalpy, entropy, and heat capacity at different temperatures. Values for polarizability, electric dipole moment, and first static hyperpolarizability have been computed. The title compound exhibits nonlinear optical properties, according to the results. In addition, Hirshfeld surface analysis was used to predict molecular interactions. Finally, molecular docking analysis of the title compound was performed. © 2025 Elsevier B.V.