Probing the Compound (E)-5-(Diethylamino)-2-[(4-Methylphenylimino)methyl]phenol Mainly from the Point of Tautomerism in Solvent Media and the Solid State by Experimental and Computational Methods

Abstract

In this study, the molecular structure and spectroscopic properties of (E)-5-(diethylamino)-2-[(4-methylphenylimino)methyl]phenol were characterized experimentally by X-ray diffraction, FT-IR and UV-vis spectroscopic techniques and computationally by DFT method. It is concluded on the basis of X-ray diffraction and FT-IR analyses that the title compound exists in enol form in the solid state. UV-vis spectra of the title compound were recorded in different organic solvents to investigate the dependence of tautomerism on solvent types. The tautomerism-solvent relation was also studied by computational methods to have more insight on structural properties. The geometry optimization of the title compound in gas phase was performed by using DFT (B3LYP) method with 6-311G(d,p) basis set. The geometry optimizations in solvent media were carried out at the same theory level by the polarizable continuum model (PCM). In the calculation of excitation energies, TD-DFT calculations were carried out in both gas and solution phases. The computational investigation of non-linear optical properties indicates that the title compound has a good second order nonlinear optical property. The thermodynamic properties were obtained in the range of 100-500 K. © 2011 Elsevier B.V. All Rights Reserved.