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Synthesis, characterization, and computational study of a new dimethoxy-chalcone

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Abstract

Chalcones are an important class of medicinal compounds and are known for taking part in various biological activities as in anti-inflammatory, anti-leishmania, antimitotic, and antiviral. Chemically, chalcones consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α,β-unsaturated carbonyl system. The wide action spectrum has attracted our attention to synthesize, crystallize, and characterize the dimethoxy-chalcone C18H18O3. Aiming to understand the process of crystal lattice stabilization, a combination of technique has been used including X-ray diffraction, infrared spectroscopy and computational molecular modeling. The theoretical calculations were carried out by the density functional method (DFT) with the M06-2X functional, with the 6-311+G(d,p) basis set. The vibrational wavenumbers were calculated and the scaled values were compared with experimental FT-IR spectrum. The intermolecular interactions were quantified and intercontacts in the crystal structure were analyzed using Hirshfeld surfaces. Bond distances and angles described by the X-ray diffraction and theoretical calculation are very similar. The C-H….O contacts contributing to assemble the supramolecular architecture are also responsible for the molecular structure assembly.

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Acknowledgments

The authors would like to acknowledge the following Brazilian agencies for financial support: Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and Fundação de Amparo Pesquisa do Estado de Goiás (FAPEG).

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Authors and Affiliations

  1. Ciências Exatas e Tecnológicas, Universidade Estadual de Goiás, CP459, 75001-970, Anápolis, GO, Brazil

    Ricardo R. Ternavisk, Ademir J. Camargo, Gilberto L. B. Aquino, Valter H. C. Silva & Hamilton B. Napolitano

  2. Departamento de Química, Instituto Tecnológico de Aeronáutica, 12228-900, São José dos Campos, SP, Brazil

    Francisco B. C. Machado & José A. F. F. Rocco

  3. Faculdade de Tecnologia SENAI Roberto Mange, 75113-630, Anápolis, GO, Brazil

    Valter H. C. Silva

Authors
  1. Ricardo R. Ternavisk
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  2. Ademir J. Camargo
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  3. Francisco B. C. Machado
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  4. José A. F. F. Rocco
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  5. Gilberto L. B. Aquino
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  6. Valter H. C. Silva
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  7. Hamilton B. Napolitano
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Corresponding author

Correspondence to Hamilton B. Napolitano.

Additional information

This paper belongs to Topical Collection Brazilian Symposium of Theoretical Chemistry (SBQT2013)

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Ternavisk, R.R., Camargo, A.J., Machado, F.B.C. et al. Synthesis, characterization, and computational study of a new dimethoxy-chalcone. J Mol Model 20, 2526 (2014). https://doi.org/10.1007/s00894-014-2526-8

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  • DOI: https://doi.org/10.1007/s00894-014-2526-8

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