Synthesis, characterization, and computational study of a new heteroaryl chalcone
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ORIGINAL PAPER
Synthesis, characterization, and computational study of a new heteroaryl chalcone Antônio S. N. Aguiar 1 & Jaqueline E. Queiroz 2 & Pollyana P. Firmino 1 & Wesley F. Vaz 1 & Ademir J. Camargo 1 & Gilberto L. B. de Aquino 1,2 & Hamilton B. Napolitano 1,3 & Solemar S. Oliveira 1 Received: 17 March 2020 / Accepted: 4 August 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract This work presents the synthesis of the chalcone (E)-3-(2,6-difluorophenyl)-1-(furan-2-yl)-prop-2-en-1-one molecule through the equimolar reaction between 1-(furan-2-yl)-ethenone and 2,6-difluorobenzaldehyde. The crystallographic characterization and the extensive theoretical study regarding electronic properties were obtained. The supramolecular arrangement was described by X-ray diffraction and Hirshfeld surfaces. Optimized geometrical structure was obtained by density functional theory, and the electronic study for differences between the solid and gas phases was carried out with M062-X at 6-311++G(2d,2p) basis set. Natural bond orbital, frontier molecular orbitals (HOMO-LUMO), and molecular electrostatic potential map were determined to elucidate the information related to the charge transfer in the molecule. The theoretical and experimental vibrational spectra were plotted, which included the IR intensities, the calculated and experimental vibrational frequencies, and the assigned vibrational modes for the main groups of DTP. Keywords DFT . X-ray diffraction . Chalcone
Introduction Chalcones are natural precursors of flavonoids which are secondary metabolites in plants [1, 2] and the yellow pigments of flowers that can be found in various parts of plants [3]. Biologically, chalcones can be defined as a class of compounds belonging to the family of phytoalexins produced during the biosynthesis of flavonoids [1] with various biological activities. In addition to natural sources, chalcones can be This paper belongs to Topical Collection XX—Brazilian Symposium of Theoretical Chemistry (SBQT2019) Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00894-020-04506-1) contains supplementary material, which is available to authorized users. * Solemar S. Oliveira [email protected] 1
Grupo de Química Teórica e Estrutural de Anápolis, Universidade Estadual de Goiás, Anápolis, GO, Brazil
2
Laboratório de pesquisa em Bioprodutos e Síntese, Universidade Estadual de Goiás, Anápolis, GO, Brazil
3
Laboratório de Novos Materiais, Centro Universitário de Anápolis, Anápolis, GO, Brazil
synthesized by different methods, such as Claisen-Schmidt aldol condensation, Wittig reactions and Friedel-Crafts acylation [4] and substitution [5], isomerization [6], and oxidative cycling methods [7]. Structurally, chalcones belong to 1,3diphenyl-2-propen-1-one skeleton group, with two aromatic rings separated by an α,β-unsaturated ketone group (–C (O)CH=CH–), which is related to their various biological activities [8, 9], such as bactericide [9], fungicide [10], antiviral [11], antiprotozoal
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