Synthesis, spectroscopy, X-ray crystallography, DFT calculations, DNA binding and molecular docking of a propargyl arms containing Schiff base

•Single crystal X-ray structure of a propargyl arms containing Schiff base.•Optimized geometries, IR and NMR spectra and NBO analysis.•Binding of the Schiff base with CT-DNA.•Molecular docking of the Schiff base with DNA.

A propargyl arms containing Schiff base (L) was synthesized by the condensation of 1-[2-hydroxy-4-(prop-2-yn-1-yloxy)phenyl]ethanone with trans-1,2-diaminocyclohexane. The structure of L was characterized by IR, 1H NMR, 13C NMR and UV–Vis spectroscopy and by single crystal X-ray diffraction analysis. The UV–Visible spectral behavior of L in different solvents exhibits positive solvatochromism. Density functional calculation of the L in gas phase was performed by using DFT (B3LYP) method with 6-31G basis set. The computed vibrational frequencies and NMR signals of L were compared with the experimental data. Tautomeric stability study inferred that the enolimine is more stable than the ketoamine form. The charge delocalization has been analyzed using natural bond orbital (NBO) analysis. Electronic absorption and emission spectral studies were used to study the binding of L with CT-DNA. The molecular docking was done to identify the interaction of L with A-DNA and B-DNA.

Graphical abstractPropargyl arms containing Schiff base (L) was synthesized. The structure of L was characterized by spectral and X-ray analysis. Molecular geometry of L was optimized by density functional method (B3LYP) with 6-31G basis set. The DNA binding ability and molecular docking were discussed.Figure optionsDownload full-size imageDownload as PowerPoint slide