Molecular structure, spectroscopic investigations and computational study on the potential molecular switch of (E)-1-(4-(2-hydroxybenzylideneamino)phenyl)ethanone

This paper presents a combined experimental and theoretical study on an ortho-hydroxy Schiff base compound, (E)-1-(4-(2-hydroxybenzylideneamino)phenyl)ethanone. The spectroscopic and electrochemical properties of the compound were determined using IR, UV–vis and 1H, 13C NMR as well as cyclic voltammetry techniques. The hydrogen bond strength was studied using the spectroscopic results, geometry calculations, topological and NBO analysis. The results showed that the predicted nonlinear optical (NLO) properties of the title compound are much greater than those of urea. Thermodynamic properties in the range from 100 to 505 K were obtained. Furthermore, molecular electrostatic potential, Fukui functions, thermodynamic, frontier molecular orbital analysis, reactivity descriptors and NLO properties were found and discussed. Theoretical results show that the conductance of the two tautomers varies seriously, which offers that this molecule has potential usage as a molecular device.