Solvents and their influence on electronic properties in IEFPCM solvation model, anticancer activity, and docking studies on (E)-2-((4-chlorobenzylidene) amino)phenol.

[Display omitted] • The highest bond length in the optimized structure was observed at 1.75 Å between C6-Cl8. • The solvent effect causes the HOMO-LUMO energy gap in the gas phase is lower (4.01 eV). • The experimental UV spectra well matched with theoretical spectra. • The titled compound showed good anticancer activity against MCF-7 cancer cell lines. • The titled compound exhibited the lowest binding energy of −5.77 kcal/mol. The Schiff base (E)-2-((4-chlorobenzylidene)amino)phenol (4CL2AM) has been synthesized from 4-chlorobenzaldehyde and 2-aminophenol. Spectroscopic techniques like FTIR, Raman, UV, fluorescence, and NMR were used to characterize the synthesized compound. The experimental data well matched with the DFT method (B3LYP/cc-pVDZ basis set). The frontier molecular orbital (FMO), molecular electrostatic potential (MEP), and electronic spectra (UV–visible) analysis were conducted on three different solvents such as gas, DMSO, and water. The frontier molecular orbital (FMO) analysis calculated the HOMO-LUMO energy gap as 4.0109 eV, 4.0406 eV, and 4.0411 eV for the gas phase, DMSO, and water respectively. Molecular electrostatic potential (MEP), localized orbital locator (LOL), and electron localize function (ELF) analysis revealed positions of localized and delocalized orbitals as well as electrophilic and nucleophilic attack sites. The natural bond orbital analysis (NBO) predicted highest stabilization energy was 33.37 kcal/mol. The locations of the covalent and non-covalent interactions were investigated by density overlaps region indicator (DORI), interaction region indicator (IRI), and noncovalent interaction (NCI) analysis. Drug likeness and ADME analysis were investigated. In vitro, anticancer activity studies revealed against MCF-7 breast cancer cell lines. In the molecular docking study, the predicted lowest binding energy is −5.77 kcal/mol for the 6NLV-4CL2AM system. [ABSTRACT FROM AUTHOR]