Abstract
The chalcones (1,3-diaryl-2-propenones) and their derivatives are important intermediates in organic synthesis and have widespread applications in medicinal industry. The title choloro chalcone derivative, 3-(3-chloro-4,5-dimethoxyphenyl)-1-(4,5-dimethoxy-2-methyl phenyl) prop-2-en-1-one, has been synthesized. It is characterized by FTIR, 1H NMR, 13C NMR and single crystal X-ray diffraction. Title compound crystallizes in monoclinic space group C2/c with a = 23.540(11) ?, b = 9.738(4) ?, c = 17.305(7) ?, β = 106.37 (3)°, V = 3806(3) ?3 and Z = 8. The mean plane of the two substituted benzene rings are twisted by 66.29 (12)° with respect to each other. Ab-initio and density functional Theory (DFT) calculations have been carried out for the title molecule using RHF/6-311G and B3LYP/6-311G basis set respectively. The calculated results show that the predicted geometry can well reproduce structural parameters. In addition, frontier molecular orbitals and Mullikan charge distributions are carried out by using RHF and B3LYP methods. The calculated HOMO and LUMO energies show that charge transfer occurs in the molecule. Numbers of weak but significant interactions like C-H···O, C-H···π and π-π are involved in the stability of the structure. The weak π-π stacked interaction involves the centroids of the methyl phenyl rings with Cg-Cg separation distance of 3.857(2) ?. Synthesized compound has been screened for its antimicrobial activity against different panels of organisms.
Highlights
In chalcones, two aromatic rings are linked by an aliphatic three-carbon chain
The quantum chemical study of the title compound has been performed within the framework of Hartree Fock [13] and the density functional theory with Becke’s three-parameter hybrid exchange functional with LeeYang-Parr correlation functional (B3LYP) employing 6-311G basis set [14,15]
Single crystal X-ray diffractions confirms the molecular structure of the title molecule, C20H21ClO5, 2-methoxy, 1-methyl substituted phenyl ring is joined by a prop-2en-1-one group to 3-chloro-4,5-dimethoxy substituted phenyl ring
Summary
Two aromatic rings are linked by an aliphatic three-carbon chain. The synthesis of chalcone derivative has generated vast interest to organics as well as for medicinal chemists. The ab-initio and density functional theory (DFT) are applied for the investigation of the optimized molecular structure and few significant spectroscopy properties. As part of our ongoing research on X-ray Crystallographic investigations of drug molecules and theoretical quantum computational studies of synthesized drugs [10,11], we have synthesized and investigated molecular structure of a novel methoxy-chloro substituted chalcone derivative by IR, NMR and X-ray diffraction techniques and optimized the structure by quantum chemistry
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