Quinolin-2(1H-)-one-isoxazole dye as an acceptor for mild addition of bisulfite in cationic or zwitterionic aqueous micellar solutions

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dc.catalogadorpva
dc.contributor.authorQuintero Faúndez, Guillermo Esteban
dc.contributor.authorEspinoza Torrealba, Catalina Paz
dc.contributor.authorValencia, Jhesua
dc.contributor.authorInsuasty, Daniel
dc.contributor.authorTiznado, William
dc.contributor.authorLeiva-Parra, Luis
dc.contributor.authorSantos Blanco, José Guillermo
dc.contributor.authorPérez Hernández, Edwin Gregorio
dc.contributor.authorAliaga Miranda, Margarita Elly
dc.date.accessioned2025-05-07T19:52:26Z
dc.date.available2025-05-07T19:52:26Z
dc.date.issued2024
dc.description.abstract(E)-6-Methoxy-1-methyl-3-(2-(3-methyl-4-nitroisoxazol-5-yl)vinyl)quinolin-2(1H)-one dye (MQI) has been synthesized, and its structural and electronic properties have been characterized by employing UV-vis spectroscopy in combination with computational methods. The MQI dye has been assessed as an activated Michael acceptor-type probe toward bisulfite ions. This reaction was kinetically tested in different mild, cationic (cetyltrimethylammonium bromide, cetyltrimethylammonium chloride, and cetylpyridinium bromide), and zwitterionic (N-decyl-N,N-dimethyl-3-ammonio-1-propanesulfonate, N-tetradecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate, and N-hexacyl-N,N-dimethyl-3-ammonio-1-propanesulfonate) micellar solutions at pH ∼ 5.5. Both micellar media remarkably allow the addition reactions, increasing the reactivity of MQI towards bisulfite ions, the biggest effects were found in the presence of cationic micelles. The binding constants of MQI with the micelles and the rate constants were determined from kinetic data, which were interpreted on the basis of the pseudophase kinetic model. The kinetic study and the product analysis allow us to highlight the relevant role of the association between MQI dye and the micellized surfactant, allowing efficient nucleophilic addition of bisulfite ions. The findings of this work will be valuable for the use of micellar solutions as an alternative medium to replace the use of toxic solvents to carry out organic reactions to perform nucleophilic addition reactions of bisulfite.
dc.fechaingreso.objetodigital2025-05-07
dc.format.extent11 páginas
dc.fuente.origenSRIA
dc.identifier.doi10.1039/d4nj03295k
dc.identifier.eissn1369-9261
dc.identifier.issn1144-0546
dc.identifier.urihttps://doi.org/10.1039/d4nj03295k
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/104077
dc.identifier.wosidWOS:001326761900001
dc.information.autorucEscuela de Química; Quintero Faúndez, Guillermo Esteban; S/I; 247028
dc.information.autorucEscuela de Química; Espinoza Torrealba, Catalina Paz; S/I; 233860
dc.information.autorucEscuela de Química; Santos Blanco, José Guillermo; S/I; 98813
dc.information.autorucEscuela de Química; Pérez Hernández, Edwin Gregorio; S/I; 191931
dc.information.autorucEscuela de Química; Aliaga Miranda, Margarita Elly; 0000-0002-4143-0301; 13361
dc.issue.numero40
dc.language.isoen
dc.nota.accesocontenido completo
dc.pagina.final17615
dc.pagina.inicio17605
dc.publisherRoyal Society of Chemistry
dc.revistaNew Journal of Chemistry
dc.rightsacceso abierto
dc.rights.licenseAttribution 3.0 Unported
dc.rights.urihttps://creativecommons.org/licenses/by/3.0/
dc.subject.ddc510
dc.subject.deweyMatemática física y químicaes_ES
dc.titleQuinolin-2(1H-)-one-isoxazole dye as an acceptor for mild addition of bisulfite in cationic or zwitterionic aqueous micellar solutions
dc.typeartículo
dc.volumen48
sipa.codpersvinculados247028
sipa.codpersvinculados233860
sipa.codpersvinculados98813
sipa.codpersvinculados191931
sipa.codpersvinculados13361
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