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

The structures of two new anthracenyl chalcones, namely (E)-1-(anthracen-9-yl)-3-(4-nitrophenyl)prop-2-en-1-one, C23H15NO3, and (E)-1-(anthracen-9-yl)-3-(4-iodophenyl)prop-2-en-1-one, C23H15IO are reported. A structural comparative study between the two chalcones was performed and some effects on th...

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Bibliographic Details
Main Authors: Dian Alwani Zainuri, Ibrahim Abdul Razak, Suhana Arshad
Format: Article
Language:English
Published: International Union of Crystallography 2018-10-01
Series:Acta Crystallographica Section E: Crystallographic Communications
Subjects:
Online Access:http://scripts.iucr.org/cgi-bin/paper?S2056989018012641
Description
Summary:The structures of two new anthracenyl chalcones, namely (E)-1-(anthracen-9-yl)-3-(4-nitrophenyl)prop-2-en-1-one, C23H15NO3, and (E)-1-(anthracen-9-yl)-3-(4-iodophenyl)prop-2-en-1-one, C23H15IO 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.
ISSN:2056-9890