Supramolecular X-ray and Quantum Chemical Analysis of 4-(2-amino-2-oxoethyl) phenyl 4-methylbenzenesulfonate: A Tosyl Ester Derivative

Abstract

4-(2-amino-2-oxoethyl) phenyl 4-methylbenzenesulfonate (APMBS), a novel compound, has been synthesized and characterized by spectro-analytical techniques. X-ray diffraction data reveals it crystallizes in the triclinic crystal system with space group \(P\overline{1}\). The structure is stabilized through strong N–H⋯O, weak C–H⋯O and C–H⋯π hydrogen bond interactions yielding a supramolecular structure. The N1A–H1AA⋯O4A, C4–H4⋯O3, and C14–H14⋯Cg1 (Ring: C8–C13) interactions link the molecules into dimers, while the interaction C9-H9–O2 results in the formation of a molecular chain along the a-axis. The optimized structural geometry, by and large, as calculated using DFT and HF techniques is in conformity with the corresponding X-ray data. The DFT computation further aid in the follow up investigations including frontier molecular orbitals (FMOs), density of states (DOS), atomic charges, and molecular electrostatic potential surface (MEP). For a comprehensive description of various molecular intersections, Hirsheld surface and fingerprint plots analysis has been reported, besides the combined atoms-in-molecules (QTAIM) and reduced density gradient (RDG) analysis. Docking studies have been performed against the target protein Tubulin-Colchicine: Stathmin-Like Domain Complex.

Graphical Abstract