Spectroscopic characterization and density functional studies of (Z)-1-[(2-methoxy-5-(trifluoromethyl)phenylamino)methylene] naphthalene-2(1H)-one

Abstract

In the current work, the Schiff base compound (Z)-1-[(2-Methoxy-5-(trifluoromethyl)phenylamino)methylenelnaphthalene-2(1H)-one (I) has been characterized by using C-13 NMR, H-1 NMR, FT-IR and UV-vis spectroscopic techniques. Molecular geometry of the compound I in the ground state, vibrational frequencies, electronic absorption spectra and gauge including atomic orbital (CIAO) H-1 and C-13 NMR chemical shift values have been calculated by using the density functional method (DFT) with 6-311++G(d,p) basis set and compared with the experimental data. The optimized geometric parameters obtained by using DFT (B3LYP/6-311++G(d,p)) show good agreement with the experimental data. The vibrational frequencies were determined based on the recorded FT-IR spectra in the range of 4000-400 cm(-1) for solid state. Using the TD-DFT method, electronic absorption spectra of the compound I have been predicted and good agreement is determined with the experimental ones. In addition, molecular electrostatic potential (MEP), frontier molecular orbital analysis (HOMO-LUMO), non-linear optical (NLO) properties. NBO analysis and NBO atomic charges of the compound I were investigated using same theoretical calculations. (C) 2015 Elsevier B.V. All rights reserved.