An Efficient Synthesis and DFT-Assisted Calculations of New 1, 2, 3-Triazole Derivatives

Abstract

Under a facial 1, 3 dipolar cycloaddition reaction, three new derivatives of 1, 2, 3-triazole (5a-c) were synthesized from azides-based anilinesulfonamide derivatives (3a-c) and pentane-2, 4-dione (4) in the presence of K₂CO₃ as a mild catalyst. The chemical structures of the synthesized 1, 2, 3-triazole (5a-c) were elucidated using different analytical techniques including ¹H and ¹³C-NMR, FT-IR, and Mass spectra. Gaussian 09 program using the functional (B3LYP/6-31G(d,p)) has been undertaken to identify the optimal geometries of the synthesized 2, 3-triazole (5a-c). The geometrical optimizations for these derivatives are conducted to DFT-assisted calculations at the same level of B3LYP/6-31G(d,p). DFT-assisted calculations were carried out to identify several important parameters including chemical hardness (η), electronic chemical potential (μ), electrophilicity (ω), and energy gap (ΔE _gap) for both molecular orbitals (LUMO and HOMO). These parameters are used as efficient descriptors for evaluating the interactions for the selected molecules and their reactivity. The results revealed that the triazole derivative (5c) is found to be more reactive than the other derivatives (5a and 5b).