Conformational Search and Spectroscopic Analysis of Biorelevant Molecule: 5-Chloro-2-hydroxy-N-isobutyl-3-oxo-2,3-dihydrobenzofuran-2-carboxamide

Abstract

The present communication deals with the conformational, vibrational spectroscopic analysis and molecular docking study of an important biorelevant molecule namely 5-Chloro-2-hydroxy-N-isobutyl-3-oxo-2,3-dihydrobenzofuran-2-carboxamide. We have recorded FTIR spectrum of the target molecule in the spectral range of 4000–400 cm−1 and this has been correlated with simulated spectra of the most stable conformer. Most of the theoretical frequencies showed good agreement with experimental frequencies and a few were modified. The theoretical computations on the target molecule have been performed at well-known DFT/B3LYP level. The 6-31++G(d,p) was incorporated as a conventional basis set during the complete computations. For normal modes analysis, the potential energy distributions of the most stable conformer were calculated by Molvib program. The NBO calculations were performed to ensure stability of electronic structure and to explore intermolecular interactions. Some important thermodynamical parameters have also been investigated. The effect of aqueous media revealed that target molecule becomes slightly more stable in water phase. HOMO-LUMO gap has been computed to be 4.19 eV.