Synthesis, X-Ray Structure Determination and Related Physical Properties of Thiazolidinone Derivative by DFT Quantum Chemical Method

In this paper we report the synthesis and characterization of the (Z)-3-N-(ethyl)-2-N'((3-methoxyphenyl)imino)thiazolidine-4-one by means of FT-IR, H-1 and C-13 NMR and by single crystal X-ray diffraction. The experimental determination of the crystal structure of the compound has been achieved using X-ray diffraction data. The important characteristic of the structure is the existence of a dihedral angle formed by the benzene and thiazolidinone rings being equal to 86.0 degrees indicating an absence of pi-pi stacking as well as that the structure is non planar. In the crystal, the molecules are linked by C-H center dot center dot center dot O and C-H center dot center dot center dot N hydrogen bonds, these bonds being responsible for the three-dimensional molecular structure packing. In order to compare the experimental results with those of the theoretical calculation, quantum chemical DFT calculations were carried out using B3LYP/6-311G(d,p) basis set. In this context, the molecular electrostatic potential around the molecule and HOMO-LUMO energy levels were also computed. The dipole moment orientations were determined in order to understand the nature of inter- and intramolecular charge transfer. Finally, the stability of the title compound was confirmed throughout the calculation of the chemical reactivity descriptors.