Spectral, quantum chemical, X-ray crystallographic, Hirshfeld surface, energy framework, and molecular docking investigations of 4-acetylphenyl 4-methylbenzenesulfonate (APMBS)

Abstract

4-acetylphenyl 4-methylbenzenesulfonate (C15H14O4S), a tosyl ester derivative, has been synthesized and characterized by spectroscopic and single crystal X-ray diffraction (SCXRD) techniques. The Hartree-Fock (HF) and the Density functional theory (DFT) methods [B3LYP/6-311 ++ G (d, p) basis set] have been employed to obtain the optimized structural geometry. The structure exhibits C—H···O type of intra- and intermolecular interactions, besides C—O···π and C—H···π interactions. The DFT calculation facilitated the exploration of frontier molecular orbitals (FMOs), Mulliken charges, density of states (DOS), and molecular electrostatic potential (MEP). A detailed Hirshfeld surface analysis has been made. Bader's atoms-in-molecules quantum theory (QTAIM) and non-covalent interaction index analysis as based on reduced density gradient (NCI-RDG) led to a quantitative description of the nature of interactions present in the crystal structure. The molecular docking has been performed against Nucleotide pyrophosphatase/phosphodiesterase (NPP) enzyme.