Synthesis, Crystallographic Structure, Hirshfeld Surface Analysis and DFT Calculations of Schiff Base (Z)-4 Phenol

Abstract

The (Z)-4-methyl-2-(((3-nitrophenyl)imino)methyl)phenol (C15H14N2O3) (MNIMP) was prepared by condensation of 2-hydroxy-5-methyl-benzaldehyde and 2-methyl-4-nitro-phenylamine in ethanol and characterized by NMR (1H and 13C), IR and UV-Visible spectroscopy. The molecular crystal packing has been quantitatively explored via Hirshfeld surface analysis, where the intramolecular C - H & ctdot;O bonding represents the principle contribution that stabilizes the crystal packing, with an overall 27.5 % for O & ctdot;H interactions. The outcomes of a theoretical investigation conducted at the B3LYP/6-311++G(d,p) level using the DFT approach are in strong agreement with the results of the experiment. The experimental outcome is compatible with the optimized structure. Z)-4-methyl-2-(((3-nitrophenyl)imino)methyl)phenol vibrational spectrum is calculated at the same theoretical level (DFT/ B3LYP/6-311++G(d,p)), and it is discovered that the theoretically estimated vibrational frequencies and assignments accord well with experimental FT-IR values.