Structural, spectroscopic characterization of 2-(5-methyl-1-benzofuran-3-yl) acetic acid in monomer, dimer and identification of specific reactive, drug likeness properties: Experimental and computational study

The spectroscopic characterization, quantum chemical, drug likeness parameters and molecular docking studies have been performed for the 2-(5-methyl-1-benzofuran-3-yl) acetic acid (2MBA) molecule. Experimental FT-IR, FT-Raman, NMR (H-1, C-13) and UV-Vis spectral studies have been compared with computationally obtained results. Computational results have been obtained in the framework of density functional theory (DFT). The dimer structure of the 2MBA have also been performed at DFT-B3LYP/6-311++ G (d, p) basis level to inspect the effect of intermolecular interactions on the molecular structure and vibrational frequencies. The geometrical parameters of 2MBA have been observed and compared with the computationally obtained parameters of both monomer and dimer at the DFT level. The harmonic vibrational wavenumbers have been obtained with the help of potential energy distribution and these were compared with the experimental (FT-IR, FT-Raman) data. The experimental NMR (H-1, C-13) chemical shifts have been compared with the chemical shifts obtained by gauge-independent atomic orbital (GIAO) method. The experimental UV-Vis spectrum of 2MBA in ethanol solution compared with theoretically obtained UV-Vis spectra in ethanol and gas phase at TD-B3LYP/6-311++ G (d, p) basis level. Natural bond orbital analyses of monomer and dimer have been performed at the DFT-B3LYP/6-311++ G (d, p) basis level. Nonlinear optical properties have also been studied by calculations of the first order hyperpolarizabilities. Frontier molecular orbitals (HOMO-LUMO), important global reactive have also been studied. The local reactivity properties of the 2MBA has been performed by using DFT computations, molecular dynamics (MD) simulations. Pharmaceutical potential of 2MBA molecule has been evaluated by calculations of the most important drug likeness parameters and by molecular docking against the selected protein. (C) 2018 Elsevier B.V. All rights reserved.