Synthesis, crystallographic and spectroscopic investigation, chemical reactivity, hyperpolarizabilities and in silico molecular docking study of (Z)-2N-(tert‑butylimino)-3N’-(4-methoxyphenyl) thiazolidin-4-one

This study presents the results related to the synthesis of (Z)-2N-(tert‑butylimino)-3N’-(4-methoxyphenyl) thiazolidin-4-one (TMTh) and its characterization by X-ray diffraction and spectroscopic techniques. The compound was characterized by 1H and 13C NMR and FT-IR spectroscopy. According to the single-crystal X-ray diffraction (SC-XRD) analysis, the title compound belongs to the centrosymmetric I2/a space group of the monoclinic system with 8 molecules in the unit cell. Using density functional theory (DFT) at the B3LYP/6-311 G (d,p) level, the optimized structure of TMTh was predicted. The structure was described by the geometric parameters confirming a good consistency between experimental and theoretical structural results. The identification of weak interactions and their contributions, including the C − H···O and C − H···S hydrogen bonds, and van der Waals (vdW) interactions, which are necessary for maintaining the crystal packing, were also addressed by the use of Hirshfeld surface (HS) and RDG analyses. From the HS, the major contribution with 56.3% is due to H···H contacts. To obtain and identify the vibration frequencies and their assignments, the PED (Potential Energy Distribution) analysis of the title compound was carried out. The results were then confirmed and compared to the experimental FT-IR spectral data. The 1H and 13CNMR chemical shifts were also calculated to compare and complement the experimental results. To highlight the compound's absorption behavior, the electronic transitions are assigned according to the time-dependent density functional theory (TD-DFT) outcomes and confirmed the electronic circular dichroism (ECD) spectrum. The experimental and theoretical UV–vis spectra are also provided suggesting a strong π→π* transition at 250 nm. Charge transfer inside the molecule was considered using the frontier molecular orbitals (FMOs) investigations, and ELF, LOL, and MEP distribution maps were also investigated. The HOMO and LUMO energies were used to estimate the chemical reactivity descriptors and the corresponding energy gap is 2.67 eV. The nonlinear optical (NLO) activity of the compound has been analyzed, and the corresponding properties have been evaluated. The most important first and second order hyperpolarizabilities calculated with BPV86 functional were found to be 5.58 × 10−30 esu and 26.01 × 10−36 esu, respectively The present study deals also with the in silico ADMET study using molecular docking and the SwissADME web tool to determine the physicochemical and pharmacokinetic properties. The biological activity was performed against the gluconate 2-dehydrogenase protein with 5U9P, 4HP8, 4Z9X, 1VL8, 4IBO and 3O03 receptors.