Structural, spectroscopic (FT-IR, FT-Raman, NMR) and computational analysis (DOS, NBO, Fukui) of 3,5-dimethylisoxazole and 4-(chloromethyl)-3,5-dimethylisoxazole: A DFT study

Abstract

The theoretical and computational analysis of two isoxazole derivatives 3,5-dimethylisoxazole and 4-chloromethyl-3,5-dimethylisoxazole were carried out along with some of the experimental evidences. The density functional theory calculations of these compounds were done with DFT/B3LYP/6-31+G(d,p) basis set using Gaussian 09 software. From the DFT calculations, the optimization geometry, vibrational analysis, electronic properties, local reactivity descriptors, natural bond orbitals, and other structural properties of the title compounds were elucidated. The chemical shifts of every C and H atom of the title compounds were calculated using Gauge Independent Atomic orbitals (GIAO) method for both proton and carbon NMR spectra. The molecular electrostatic potential of DMI has been found out and the difference in MEP on addition of chloromethyl group is also discussed. The hyperpolarizability calculations of the investigated molecules shows that the nonlinear optical activity of CDMI is greater when compared to DMI.