Synthesis, structural features, excited state properties, flouresence spectra, and quantum chemical modeling of (E)-2-hydroxy-5-(((4-sulfamoylphenyl)imino) methyl)benzoic acid

Abstract

• Synthesis of a new Schiff base from 5-formylsalicylic acid and sulfanilamide. • Spectral characterization reported. • Compound showed excellent Fluorescence as evident from fluorescence spectra. • Detailed vibrational studies and other theoretical analysis done. • Compound found to be a NADPH peroxidase inhibitor with the help of docking studies. The structure, spectroscopic features, and pharmaceutical effect of (E)-2-hydroxy-5-(((4-sulfamoylphenyl)imino)methyl)benzoic acid (E7) has been studied by density functional theory modeling, infrared, FT-Raman, 1 H and 13 C NMR, and molecular docking investigation. Molecular structure analysis was carried out using DFT calculation. Then, the low RMSD value indicates the good agreement between calculated and observed data. In order to understand the electronic charge transition, the electron difference density technical was performed. 1 H and 13 C NMR spectra were recorded in the region of 0–15 and 5–225 ppm, respectively, and FT-IR and FT-Raman spectra’s of E7 was obtained from 4000 to 500 cm-1 and 4000 to 50 cm-1. Electronic structure characteristics were achieved at the level of B3LYP/cc-PVDZ. Inter and intramolecular interactions are discussed by topological (Electron localized function, Localized orbital locator, average localized ionization energy and non-covalent interaction). Time dependent density functional theory calculations were conducted to reveal molecular orbital based reactivity characteristics. Molecular docking of the title compound was carried. Docking simulation shows the potential of E7 against NADPH peroxidase inhibitor receptor.