Synthesis, spectroscopic characterization (FT-IR, NMR) and DFT computational studies of new isoxazoline derived from acridone

• Published in: Journal of molecular structure 2021-05, Vol.1231, p.129921, Article 129921
• Main Authors: Aarjane, Mohammed, Slassi, Siham, Ghaleb, Adib, Amine, Amina
• Format: Article
• Language: English
• Subjects: Acridone; FT-IR; Isoxazoline; MESP; Mulliken charge; NMR
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2021.129921

•10‐{[3‐(4‐chlorophenyl)‐4,5‐dihydro‐1,2‐oxazol‐5 yl]methyl} acridone was synthesized using an efficient and regioselective synthetic route.•The compound (3) was characterized with 1H & 13C NMR, FT-IR and HRMS.•Density Functional Theory (DFT) method with 6–31G(d,p) base sets was used for theoretical studies.•Spectral data were compared with computational ones.•Molecular electrostatic potential (MEP) and frontier molecular orbitals (FMOs) analysis were done. In this study, a new isoxazoline derived from acridone, 10‐{[3‐(4‐chlorophenyl)‐4,5‐dihydro‐1,2‐oxazol‐5 yl]methyl} acridone (3) was successfully synthesized and characterized by FT-IR, 1H NMR, 13C NMR and HRMS. The preparation of compound (3) was achieved by 1,3-dipolar cycloaddition reaction between 4‑chloro-N-hydroxybenzimidoyl chloride and 10-allylacridone using environment friendly methods. In an effort to complete the chemical structure description of the synthetized compound, Density Functional Theory (DFT) was applied using Gaussian09 and Gaussian view5 programs. The theoretical calculations were used as a compliment to the experimental studies. The computing of geometric parameters, optimization energies, frontier molecular orbital energies, Molecular surface electrostatic potential (MESP) and Mulliken charges were calculated using DFT/B3LYP method with 6–31G(d,p) as basis set. The Infrared vibrational frequencies and 1H and 13C NMR chemical shifts were also calculated and their scaled values are in agreement with the experimental results. [Display omitted]