Synthesis, Spectroscopic Characterization, and DFT Computational Study of a Novel Benzimidazole-Based Imidazolidinone Derivative
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https://doi.org/10.37022/jcls.v9i1.231Keywords:
Benzimidazole, Imidazolidinone, [2 3] Cycloaddition, DFT, B3LYP, Fukui Functions, Global Reactivity DescriptorsAbstract
A novel benzimidazole-based imidazolidinone derivative, namely 3-(2-(5-chloro-1H-benzo[d]imidazol-2-yl)phenyl)-2-(3-hydroxy-2-methoxyphenyl)-5-methylimidazolidin-4-one (1), was synthesized via [2+3] cycloaddition reaction between a Schiff base precursor and alanine in 1,4-dioxane under reflux conditions. The structure of the synthesized compound was confirmed by FT-IR, 1H NMR, and 13C NMR spectroscopic techniques. The FT-IR spectrum exhibited characteristic absorption bands at 3363 cm⁻¹ (N–H), 1681 cm⁻¹ (C=O), and 1596 cm⁻¹ (C=C aromatic), confirming the formation of the imidazolidinone ring. Density functional theory (DFT) calculations were performed at the B3LYP/6-31G(d) level of theory on a geometry optimized by GFN2-xTB. The HOMO–LUMO energy gap was found to be 4.8685 eV, indicating moderate kinetic stability and chemical reactivity. Global reactivity characteristics such as electronegativity (χ=3.5583eV), chemical hardness (η=2.4343eV) and electrophilicity index (ω=2.6006eV) were calculated by utilising Koopmans' theorem. The most reactive sites for nucleophilic and electrophilic assault have been determined by Mulliken population analysis and Fukui function calculations. The dipole moment was calculated to be 3.9053 Debye which indicates the substantial polarity of molecule.
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