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Analysis of two novel 1–4 quinolinone structures with bromine and nitrobenzyl ligands

  • Lidiane J. Michelini
  • Wesley F. Vaz
  • Giulio D. C. D’Oliveira
  • Caridad N. Pérez
  • Hamilton B. NapolitanoEmail author
Original Paper
  • 7 Downloads

Abstract

The scientific community has shown particular interest in the study of quinolinones—a class of bicyclic organic compounds. An example of these compounds are the 4-quinolinones, considered to be very useful building blocks, since they can adapt their molecular structures with different ligands for applications in various fields such as pharmacy, medicine, physics and engineering. The compounds (E)-3-(benzylidene)-2-(3-nitrophenyl)-2,3-dihydro-1-(phenylsulfonyl)-quinolin-4-(1H)-one (NFQ) and (E)-3-(benzylidene)-2-(4-bromophenyl)-2,3-dihydro-1-(phenylsulfonyl) quinolin-4-(1H)-one (BFQ) were synthesized and characterized by infrared spectroscopy, 1H and 13C NMR, and melting point. NFQ crystallized in the orthorhombic Pbca space group while BFQ appears in the monoclinic P21/n space group. X-ray diffraction was used to evaluate their crystallographic structures, and Hirshfeld surface evaluates the intermolecular interactions, supramolecular arrangement and packaging. Theoretical vibrational assignments and calculated electronic properties also demonstrate acceptable agreement between experimental and theoretical results.

Keywords

DFT X-ray diffraction Hirshfeld surface Quinolinone 

Notes

Acknowledgments

The authors would like to thank Brazilian funding agencies Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) and Fundação de Amparo à Pesquisa do Estado de Goiás (FAPEG) for financial support and fellowships. Research developed with support of the High-Performance Computing Center at the Universidade Estadual de Goiás (UEG). Single crystal X-ray diffraction data were collected at Universidade de São Paulo (USP).

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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Instituto de QuímicaUniversidade Federal de GoiásGoiâniaBrazil
  2. 2.Instituto Federal de CiênciaEducação e Tecnologia GoianoIporáBrazil
  3. 3.Ciências Exatas e TecnológicasUniversidade Estadual de GoiásAnápolisBrazil

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