Leacture

Abstract
In this study, outline the synthesis and spectroscopic characterization of novel 2-imino-thiazolidin-4-one derivatives. The synthesis process is divided into three main parts. Firstly, we prepared the starting material, 2-\r\namino-4-(substitutedphenyl)-1,3-thiazole, by reacting thiourea with substituted acetophenone in the presence\r\nof iodine. The second part involved the synthesis of 2-chloroacetamido-4-(substitutedphenyl)-1,3-thiazole\r\nthrough the reaction of heterocyclic amine with chloroacetyl chloride in benzene. The third part focused on\r\nthe cyclization reaction of synthesized intermediate compounds, leading to the formation of a new series of\r\ndesired products, namely, 2-imino-3-[4-(substitutedphenyl)-1,3-thiazol-2-yl] thiazolidin-4-ones. The structures\r\nof the synthesized compounds were determined based on spectral data, including IR, 1\r\nHNMR, and 13CNMR.\r\nVarious analytical methods were employed to explore intermolecular interactions, nonlinear optical properties,\r\nHOMO-LUMO energy gap, potential energy maps, Natural Bond Orbital (NBO) analysis, and thermodynamic\r\nparameters of diverse compounds. The assessment of weak intermolecular interactions using Noncovalent interactions (NCI) and reduced density gradient (RDG) methods revealed the presence of robust hydrogen bonds,\r\nvan der Waals forces, and steric effects within the compounds. Topological parameters highlighted significant\r\nhydrogen bonding capabilities among the studied compounds. Additionally, the analysis of the HOMO-LUMO\r\nenergy gap and other quantum chemical parameters unveiled the influence of protonation on polarization,\r\nchemical reactivity, and corrosion resistance. Molecular Electrostatic Potential (MEP) analysis indicated changes\r\nin electrophilicity and nucleophilicity upon the addition of protons, altering chemical reactivity. Stabilization\r\nenergies of donor-acceptor interactions, assessed through Natural Bond Orbital (NBO) analysis, provided insights\r\ninto charge transfer and conjugative interactions, particularly emphasizing electron delocalization within the\r\ncompounds’ phenyl rings.

Author
Rebaz Anwar OMER

DOI
https://doi.org/10.1016/j.molstruc.2024.138055

ISSN
0022-2860

Publish Date: 2024-03-20