Crystal structure, spectroscopic characterization and DFT study of two new linear fused-ring chalcones

Abstract

The structures of two new anthracenyl chalcones, namely (E)-1-(anthracen-9-yl)-3-(4-nitrophenyl)prop-2-en-1-one, C 23 H 15 NO 3, and (E)-1-(anthracen-9-yl)-3-(4-iodophenyl)prop-2-en-1-one, C 23 H 15 IO are reported. A structural comparative study between the two chalcones was performed and some effects on the geometrical parameters, such as planarity and dihedral angles, are described. The molecular geometry was determined by single-crystal X-ray diffraction, and density functional theory (DFT) at B3LYP with the 6-311++G(d,p) basis set was applied to optimize the ground-state geometry. In addition, intermolecular interactions responsible for the crystal packing were analysed. The electronic properties, such as excitation energies and HOMO-LUMO energies were calculated by time-dependent density functional theory (TD-DFT) and the results complement the experimental findings. The molecular electrostatic potential (MEP) was also investigated at the same level of theory in order to identify and quantify the possible reactive sites.