Synthesis, structure, spectroscopic (FT-IR) and density functional modelling studies of 1-[(4-ethoxyphenylimino)methyl]napthalene-2-ol

Synthesis, crystallographic characterisation, spectroscopic (Fourier transform infrared spectroscopy [FT-IR]) and density functional modelling studies of the Schiff base 1-[(4-ethoxyphenylimino)methyl]napthalene-2-ol (C19H17NO2) have been reported. The molecular structure obtained from X-ray single-crystal analysis of the investigated compound in the ground state has been compared using Hartree-Fock and density functional theory (DFT) with the 6-311++G(d,p) basis set. In addition to the optimised geometrical structures, atomic charges, molecular electrostatic potential, natural bond orbital, non-linear optical (NLO) effects and thermodynamic properties of the compound have been investigated by using DFT. The experimental (FT-IR) and calculated vibrational frequencies (using DFT) of the title compound have been compared. The solvent effect was also investigated for obtained molecular energies and the atomic charge distributions of the compound. There exists a good correlation between experimental and theoretical data for enol-imine form of the compound. The total molecular dipole moment (µ), linear polarisability (?), and the first-order hyperpolarisability (ß) were predicted by the B3LYP method with different basis sets 6-31G(d), 6-31+G(d,p), 6-31++G(d,p), 6-311+G(d) 150 and 6-311++G(d,p) for investigating the effects of basis sets on the NLO properties. Our computational results yield that ßtot for the title compound is greater than those of urea. © 2014 Taylor & Francis.Türkiye Atom Enerjisi KurumuaDepartment of Training and Application, Ankara Nuclear Research and Training Center, Turkish Atomic Energy Authority, Besevler-Ankara, Turkey; bDepartment of Physics, Faculty of Sciences and Arts, University of Aksaray, Aksaray, Turkey; cDepartment of Chemistry, Faculty of Sciences and Arts, C¸ anakkale Onsekiz Mart University, C¸ anakkale, Turkey; dDepartment of Physics, Faculty of Sciences, University of Ankara, Besevler-Ankara, TurkeyThis work was supported by the State of Planning Organization [grant number 2010K120480]