Synthesis, Spectroscopic Characterization and Computational Studies of (Z)-1

Abstract

The Schiff base compound (Z)-1-((5,6,7,8-tetrahydronaphthalen-1-ylamino) methylene)naphthalen-2(1H)-one has been synthesized and characterized by IR, UV-Vis and single-crystal X-ray diffraction. The title compound exist as NH tautomeric form in solid state. Molecular geometry and vibrational frequencies of the 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 structural parameters, and the theoretical vibrational frequencies are in good agreement with the experimental values. In calculation of electronic absorption spectra, TD-DFT calculations were carried out in the both gas and solution phases. The energetic behavior of the compound in solvent media has been examined using B3LYP method with the 6-31G(d,p) basis set by applying the polarizable continuum model (PCM). The total energy of the compound decreases with increasing polarity of the solvent. Besides, molecular electrostatic potential (MEP), non-linear optical (NLO) properties of the compound were investigated using theoretical calculations. © 2013 Elsevier B.V. All rights reserved.