Combined X-ray, IR, intramolecular proton transfer and quantum chemical studies on (E)-2-Bromo-4-methoxy-6-[(p-tolylimino)methyl]phenol

Abstract

In this work, molecular and crystal structure of (E)-2-Bromo-4-methoxy-6-[(p-tolylimino) methyl] phenol which is an o-hydroxy Schiff base derivative was characterized by X-ray single crystal diffraction, IR spectroscopy. In the quantum mechanical calculations, the density functional theory (B3LYP) with 6-31G (d, p) was used to support our studies. According to the X-ray crystallographic data, the title compound adopted the phenol-imine tautomeric form in solid state. The two possible tautomeric forms of the title compound were investigated using DFT method with B3LYP applying 6-31G(d, p) basis set. A relaxed potantial energy surface (PES) scan was performed based on the optimized geometry of the OH tautomeric form and O–H bond distances were used as the redundant internal coordinate. PES scan process was helped us for understand the effects of transfer on the molecular geometry. At the same time, in this study, we were investigated nonlinear optical properties (NLO) of the title molecule.