Synthesis, characterization and conformational analysis of two novel 4(1H)‑quinolinones
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2020
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Quinolinones are a class of organic compounds known as alkaloids found in several plants and
also can be synthesized. Their large use in therapies regards their wide biological potential like
antitumor, psychiatric and neurological agents. Two substances were structurally characterized:
(E)-3-(2-nitrobenzylidene)-2-(4-methoxyphenyl)-1-(phenylsulfonyl)-2,3-dihydroquinolin4(1H)-one (NMQ), and (E)-3-(2-chlorobenzylidene)-2-(2-methoxyphenyl)-1-(phenylsulfonyl)-
2,3-dihydroquinolin-4(1H)-one (CMQ). These compounds were synthesized, crystallized,
characterized by single crystal X-ray diffraction and theoretical calculations. The NMQ and
CMQ crystals are formed by a pair of enantiomers and crystallized in the centrosymmetric group
P21/c with similar volume and density. Differences noted on crystal packing and supramolecular
arrangement are associated to substituent group chlorine in CMQ and nitro in NMQ. The calculated
infrared (IR) spectra show a good agreement with experimental values. The highest occupied
molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies show CMQ
more kinetically stable with a higher resistance to transfer charge than NMQ.
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Quinolinones, X-ray diffraction, Theoretical analysis
Citação
MICHELINI, Lidiane J. et al. Synthesis, characterization and conformational analysis of two novel 4(1H)‑quinolinones. Journal of the Brazilian Chemical Society, Campinas, v. 31, n. 1, p. 66-78, 2020. DOI: 10.21577/0103-5053.20190124. Disponível em: https://jbcs.sbq.org.br/default.asp?ed=293. Acesso em: 24 ago. 2023.