Synthesis, crystal structure, hirshfeld surface analysis, DFT computations and molecular dynamics study of 2-(benzyloxy)-3-phenylquinoxaline

Quinoxalines are regarded as a promising class of biologically active agents, and they constitute useful intermediates in organic synthesis. In this study, we report synthesis, single crystal X-ray diffraction, and computational investigations of the 2-(benzyloxy)-3-phenylquinoxaline (O-alkylated isomer). Single crystal X-ray diffraction investigations revealed that the quinoxaline unit is not entirely planar. In the crystal form, inversion-related molecules form dimers through slipped ?-stacking interactions between quinoxaline units. These are coupled together into chains extending along the c-axis direction by C–H···?(ring) interactions. Inspection of the Hirshfeld surface analysis revealed that H?H (48.8%), C?H/H?C (35.1%) and H?N/N?H (7.3%) are the main interactions that govern the crystal packing of the presented structure. The optimized geometry, Natural Bond Orbital (NBO), Fukui functions and all other structural and electronic features were calculated by using Density Functional Theory (DFT) at B3LYP employing 6–311++G(d,p) basis set. The HOMO and LUMO distribution showed a pronounced electronic density over the quinoxaline moiety. Computed NBO analysis explored the interactions as well as charge transfers among different orbitals and lone pairs occurring within the compound. Radial distribution functions (RDF) were calculated using molecular dynamics (MD) simulations to study interactions of water molecules with atoms of the title compound.