Synthesis and Characterization of Ionic Liquid Supported on Fe₃O₄ Nanoparticles and a DFT Study of 1,3-Dipolar Cycloaddition for the Synthesis of Isoxazolidines in the Presence of Ionic Liquid-Fe₃O₄

GRAPHICAL ABSTRACT

Synthesis and characterization of ionic liquid (IL) supported on Fe₃O₄ nanoparticles and a DFT study of 1,3-dipolar cycloaddition for synthesis of isoxazolidines in the presence of IL-Fe₃O₄.

ABSTRACT

A family of novel ionic liquid (IL) with L-alanine and choline chloride as environmentally benign materials has been synthesized and grafted on Fe₃O₄ nanoparticles (NPs) using easy preparation techniques. The structure of IL supported on Fe₃O₄ NPs (IL-Fe₃O₄ NPs) is characterized by various techniques such as field emission scanning electron microscopy (FE-SEM), Energy Dispersive X-Ray (EDX), XRD, Nuclear Magnetic Resonance (NMR), Fourier Transform Infrared (FTIR), and vibrating sample magnetometry (VSM). A stereoselective synthesis of isoxazolidine derivatives in good yields, through a three-component 1,3-dipolar cycloaddition reaction using by IL-Fe₃O₄ NPs, is reported. The use of IL-Fe₃O₄ as a catalyst allowed us to prepare diastereoselective isoxazolidine derivatives. Conformational analysis compared with the ¹H NMR data of the products obtained allowed us to determine the absolute configuration. In this paper, the density functional theory (DFT) method with 6-311G (d,p) basis set is employed for solution phase (solvent = CHCl₃) of the isoxazolidine derivatives.

KEYWORDS:

• DFT study
• Fe₃O₄ nanoparticles
• ionic liquid
• isoxazolidines

Acknowledgment

The authors are grateful to the University of Kashan for supporting this work.