Synthesis, Characterization, Hirshfield Surface Analysis and DFT Calculation of (2Z,5Z)-3

Abstract

The crystal (2Z,5Z)-3-(2-methoxyphenyl)-2-[(2-methoxyphenyl)imino]-5-(3-nitrobenzylidene) thiazolidin-4-one, abbreviated as MMINT, was synthesized and characterized using single-crystal XRD and two spectroscopic techniques, FT-IR and NMR. Using Hirshfeld surface analysis, the stability of the crystal structure was investigated. The results showed that the main contributors to the intermolecular forces stabilizing the crystalline structure are H center dot center dot center dot H interactions (35.1%), O center dot center dot center dot H/H center dot center dot center dot O (23.7%), and C center dot center dot center dot H/H center dot center dot center dot C (23.5%) interactions. To support experimental results, density functional theory with the B3LYP/6-311++G(d,p) level of theory was employed to optimize geometrical parameters and compare them with the experimental results. Local and global chemical reactivity descriptors are then calculated and discussed to interpret reactivity features across a diverse range of chemical reactions. Excellent agreement between the density functional theory calculations and the experimental data was seen upon investigation of the acquired results. This compound exhibits more stability and less reactivity at high polar media. Fukui function analysis indicates a susceptibility of this molecule to nucleophilic and electrophilic attacks. Furthermore, natural bond orbital analysis shows that interactions between heteroatoms and aromatic rings contribute to the stabilization of the studied compound.