Single‐Crystal, Supramolecular, and DNA‐Binding Investigations of a Schiff Base Derived From 2,4‐Dimethylaniline

ABSTRACT

Herein, a new Schiff base ( E )‐1‐(((2,4‐dimethylphenyl)imino)methyl)naphthalen‐2‐ol ( DM‐ND ) has been synthesized by condensing 2,4‐dimethylaniline and 2‐hydroxy‐1‐naphthaldehyde in absolute ethanol. The synthesized Schiff base was characterized by a variety of spectroscopic techniques, such as FT‐IR, NMR ( ¹ H and ¹³ C), and combustion (CHN) analysis. Furthermore, single‐crystal x‐ray diffraction (SC‐XRD) studies were used to investigate its molecular structure. It was confirmed from the solid‐state x‐ray diffraction analysis that the asymmetric unit contained only one Schiff base molecule, which adopted a keto tautomeric form. The crystal packing is stabilized by C─H···O, C─H···π, and π···π interactions, whose occurrence and relative surface contributions were further examined using Hirshfeld surface analysis. Density functional theory (DFT)‐based quantum mechanical calculations were employed to validate the molecular geometry and to evaluate important electronic properties, including HOMO–LUMO gap, molecular electrostatic potential (MEP), infrared, and UV–visible absorption spectra. Molecular docking simulations, performed with the neutral keto tautomer of DM‐ND , predicted a favorable docking score of −7.7 kcal/mol for binding within the DNA minor groove, suggesting DM‐ND as a candidate for further evaluation as a DNA‐interacting agent.