Synthesis, characterization, and electronic structure of bioactive vanillin based fluorescent Schiff bases

Abstract

This manuscript presents a comprehensive investigation into the Synthesis, characterization, and molecular properties of a novel compound, (E)-2-methoxy-4-((phenylimino)methyl)phenol, referred to as ANVA. The synthesis procedure involved the reaction of vanillin and aniline, which resulted in the formation of ANVA. Various analytical techniques, including FTIR, fluorescence, UV–Vis, 1HNMR, and 13CNMR, were employed to characterize the compound's structural and spectral properties. We conducted theoretical investigations using DFT/B3LYP/cc-pVDZ techniques to gain insights into the compound's electronic structure, stability, and reactivity. Molecular Electrostatic Potential (MEP) analysis elucidated the molecule's polarity and revealed potential nucleophilic attack sites. Mulliken population analysis showed the distribution of electrical charges among atoms, influencing various chemical properties. Quantum Theory of Atoms in Molecules (QTAIM) analysis, including ELF and LOL, provided a deeper understanding of electron localization and delocalization, shedding light on covalent bonds and molecular stability. The study also explored non-covalent interactions through Reduced Density Gradient (RDG) analysis, indicating weak and strong interactions within the compound. Molecular docking studies were performed to assess the potential biological activity of ANVA, yielding significant insights into its interaction with specific protein targets.