Experimental and computational studies on zwitterionic (E)-1-((4-phenoxyphenyliminio)methyl)naphthalen-2-olate

The Schiff base compound (E)-1-((4-phenoxyphenyliminio)methyl)naphthalen-2-olate has been synthesized and characterized by IR, UV–Vis, and X-ray single-crystal determination. lar geometry of the title compound in the ground state have been calculated using the density functional method (DFT) with 6-31G(d,p) basis set and compared with the experimental data. The calculated results show that the optimized geometry can well reproduce the crystal structure. By using TD-DFT method, electronic absorption spectra of the title compound have been predicted and a good agreement with the TD-DFT method and the experimental ones is determined. Molecular orbital coefficient analyses reveal that the electronic transitions are mainly assigned to n → p∗ and p → p∗ electronic transitions. To investigate the tautomeric stability, optimization calculations at B3LYP/6-31G(d,p) level were performed for the NH and OH forms of the title compound. Calculated results reveal that the OH form is more stable than NH form. In addition, molecular electrostatic potential and non-linear optical properties of the title compound were performed at B3LYP/6-31G(d,p) level of theory.