Experimental and Theoretical Investigation on Imidazole Derivatives Using Magnetic Nanocatalyst: Green Synthesis, Characterization, and Mechanism Study
Creators: name: Nasehi, Niloufar
name: Mirza, Behrooz
name: Soleimani-Amiri, Somayeh
Publisher: name: Taylor & Francis
Year: 2022
Subjects: subject: Biophysics
subject: Biochemistry
subject: Cell Biology
subject: Molecular Biology
subject: Physiology
subject: FOS: Biological sciences
subject: Chemical Sciences not elsewhere classified
subject: Biological Sciences not elsewhere classified

description: The green synthesis of 4,5-diphenyl-1H-imidazole derivatives was studied experimentally and theoretically through a one-pot, three-component reaction of diverse aldehydes, ammonium acetate, and benzil using Fe<sub>3</sub>O<sub>4</sub>@C@PrNHSO<sub>3</sub>H nanoparticles under solvent-free conditions. The core-shell magnetic nanoparticles of Fe<sub>3</sub>O<sub>4</sub>@C@PrNHSO<sub>3</sub>H were introduced as an effective, environmentally friendly, and magnetically removable catalyst in the reaction. The recovered catalyst could be used eight times with admirable catalytic activity. Before entering the laboratory, the synthesis of imidazoles was studied from a computational point of view to find the most plausible mechanism and select the appropriate raw materials. Three probable mechanistic paths were considered. Density functional theory (DFT) calculations confirmed the following mechanism: (1) reaction of benzil and ammonia to form iminoethanone, (2) reaction of aldehyde and ammonia to form imin, (3) reaction of imin with iminoethanone and ring formation, and (4) rearrangement to produce 4,5-triphenyl-1H-imidazole. The results were affirmed by the frontier molecular orbitals, natural bond orbital analyses, and molecular electrostatic potential calculations.HIGHLIGHTSThe green synthesis of 4,5-diphenyl-1H-imidazole derivatives was studied experimentally and theoretically using Fe<sub>3</sub>O<sub>4</sub>@C@PrNHSO<sub>3</sub>H nanoparticles (NPs).Three proposal mechanisms were considered using M062X/6-311++G(d,p) to achieve the most plausible mechanism,The proposed mechanism was verified by the frontier molecular orbitals, natural bond orbital analyses, and molecular electrostatic potential calculations.The Fe<sub>3</sub>O<sub>4</sub>@C@PrNHSO<sub>3</sub>H NPs were introduced as an effective, eco-friendly and magnetically recoverable catalyst in the one-step synthesis of imidazoles.The recovered catalyst could be used eight times with admirable catalytic activity. The green synthesis of 4,5-diphenyl-1H-imidazole derivatives was studied experimentally and theoretically using Fe<sub>3</sub>O<sub>4</sub>@C@PrNHSO<sub>3</sub>H nanoparticles (NPs). Three proposal mechanisms were considered using M062X/6-311++G(d,p) to achieve the most plausible mechanism, The proposed mechanism was verified by the frontier molecular orbitals, natural bond orbital analyses, and molecular electrostatic potential calculations. The Fe<sub>3</sub>O<sub>4</sub>@C@PrNHSO<sub>3</sub>H NPs were introduced as an effective, eco-friendly and magnetically recoverable catalyst in the one-step synthesis of imidazoles. The recovered catalyst could be used eight times with admirable catalytic activity.