Synthesis, characterization, and computational study of a new dimethoxy-chalcone
Ricardo R Ternavisk1, Ademir J Camargo, Francisco B C Machado
1Ciências Exatas e Tecnológicas, Universidade Estadual de Goiás, CP459, 75001-970, Anápolis, GO, Brazil.
Journal of Molecular Modeling
|November 26, 2014
Summary
This study synthesized and characterized dimethoxy-chalcone, revealing that C-H….O contacts stabilize its crystal structure. These interactions are crucial for both supramolecular architecture and molecular assembly in medicinal compounds.
Area of Science:
- Medicinal Chemistry
- Crystallography
- Computational Chemistry
Background:
- Chalcones are vital medicinal compounds with diverse biological activities, including anti-inflammatory and antiviral properties.
- Structurally, chalcones are open-chain flavonoids featuring two aromatic rings linked by an α,β-unsaturated carbonyl system.
Purpose of the Study:
- To synthesize, crystallize, and characterize a specific dimethoxy-chalcone (C18H18O3).
- To investigate the factors contributing to crystal lattice stabilization using experimental and computational methods.
Main Methods:
- Synthesis and crystallization of dimethoxy-chalcone.
- X-ray diffraction and Fourier-transform infrared (FT-IR) spectroscopy for experimental characterization.
- Density Functional Theory (DFT) calculations with M06-2X functional and 6-311+G(d,p) basis set for theoretical analysis.
- Hirshfeld surface analysis to quantify intermolecular interactions.
Main Results:
- Experimental and DFT calculations showed highly similar bond distances and angles.
- Calculated vibrational wavenumbers closely matched the experimental FT-IR spectrum.
- Hirshfeld surface analysis identified C-H….O contacts as key drivers of supramolecular and molecular assembly.
Conclusions:
- The study successfully characterized dimethoxy-chalcone and elucidated its crystal structure stabilization mechanisms.
- C-H….O intermolecular interactions play a critical role in the assembly of the chalcone's supramolecular architecture and molecular structure.
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