Synthesis, crystal structure analysis, spectral characterization, quantum chemical calculations, antioxidant and antimicrobial activity of 3-(4-chlorophenyl)-3a,4,7,7a-tetrahydro-4,7-methanobenzo[d]isoxazole

Abstract

In this paper, 3-(4-chlorophenyl)-3a,4,7,7a-tetrahydro-4,7-methanobenzo[d]isoxazole was synthesized via 1,3 dipolar cycloaddition, characterized by spectroscopic analysis such as FT-IR, 1H NMR, 13C NMR, UV-Vis, LC-MS/MS, Elemental Analysis, and X-ray Single Crystal diffraction technique. The Density Functional Theory (DFT/B3LYP) method with 6-311G(d,p) basis set in the ground state was applied for quantum chemical calculations and molecular geometric parameters of the compound were compared with the X-ray analysis results. FT-IR, NMR and UV–Vis spectral analysis were analysed to determine the compliance with the vibrational frequencies, 1H NMR and 13C NMR chemical shifts and absorption wavelength values. The frontier molecular orbitals (FMOs), some global reactivity descriptors, molecular electrostatic potential (MEP), thermodynamic properties, non-linear optical (NLO) behaviour of the compound were examined with the same method in gas phase, theoretically. Moreover, antioxidant activity was determined with three different methods - DPPH radical scavenging, reducing and metal chelating, antimicrobial activity were carried out with Gram positive, Gram negative and Eukaryote for the title compound.