Synthesis, IR and NMR–Spectroscopic, DFT Study of Aroyl Hydrazones ۴,۴,۴-Trifluoro-۱-(۳-Furanyl)-۱,۳-Butanedione

Aroyl hydrazones derived from ۴,۴,۴-trifluoro-۱-(۳-furanyl)-۱,۳-butanedione represent a structurally distinctive and chemically significant class of organic compounds with considerable potential for application in various fields, including coordination chemistry, spectroscopy, and medicinal chemistry. These compounds exhibit versatile chelating behavior and are of great interest due to their pronounced biological activity. In the present study, a series of aroyl hydrazones was successfully synthesized via condensation of substituted acid hydrazides with the trifluoroacetyl moiety of the β-diketone precursor. Structural elucidation was carried out using Fourier-transform infrared (FTIR) spectroscopy, ۱H and ۱۳C nuclear magnetic resonance (NMR) techniques, and theoretical methods based on density functional theory (DFT). Experimental data correlated well with DFT-optimized structures, confirming the predominance of the hydrazone tautomer. Theoretical calculations also provided HOMO-LUMO energy levels, dipole moments, molecular electrostatic potential (MEP) maps, and Mulliken charge distributions. Molecular docking studies revealed energetically favorable binding interactions with P. aeruginosa target proteins. Molecular docking of the H۲L۱ ligand with the ۱U۱Z protein exhibited strong binding interactions (–۱۱.۶۲۵۵ kcal/mol) via hydrogen bonds, π-π, and π-anion contacts, suggesting promising biological activity. Taken together, the findings of this study underline the potential applicability of these hydrazones as ligands for metal complexation and as promising bioactive compounds.

کلیدواژه ها:

hydrazone ، DFT ، HOMO ، LUMO ، Molecular docking