2-thioxo -3N-(2-ethoxyphenyl) -5[4′-methyl -3′N-(2′-ethoxyphenyl) thiazol-2′(3′H)-ylidene] thiazolidin-4-one: Growth, spectroscopic behavior, single-crystal investigation, Hirshfeld surface analysis, DFT/TD-DFT computational studies and NLO evaluation

Abstract

In this work, 2-thioxo -3 N-(2-ethoxyphenyl -5[4′-methyl -3′N-(2′-ethoxyphenyl) thiazol-2′(3′H)-ylidene] thiazolidin-4-one (E2Th2) was synthesized and its molecular structure determined by FT-IR, UV-Vis and NMR spectroscopic techniques along with a single crystal X-ray diffraction study. Quantum chemical calculations were performed to better understand its structural, spectroscopic and electronic properties such as HOMO and LUMO energy gap, MEP and global reactivity descriptors. Theoretical calculations were performed using density functional theory (DFT) based on the B3LYP/6-311G (d,p). Vibrational frequencies were assigned on the basis of PED and electronic transitions are calculated according to time-dependent density functional theory (TD-DFT). The HOMO and LUMO analysis are used to determine the charge transfer within the molecule. The NLO activity evaluation was based on the determination of the dipole moment, polarizability (α), first-order hyperpolarizability (β) and the second-order hyperpolarizability (γ) which were calculated using the same level of theory. The hyper-hardness descriptor (Γ) was explored and correlated with the NLO properties. Additionally, the stability of the molecule occurring from hyper-conjugative interaction, intramolecular hydrogen bond and charge delocalization were quantified using NBO analysis. The repulsive, attractive, and van der Waals strong and weak interactions were revealed by RDG and HS analyses. Finally, results have shown that the title compound can be used as attractive future NLO material.