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Authordc.contributor.authorFuente, J. de la 
Authordc.contributor.authorCañete Molina, Alvaro Félix es_CL
Authordc.contributor.authorZanocco Loyola, Antonio es_CL
Authordc.contributor.authorSaitz Barría, Claudio es_CL
Authordc.contributor.authorJullian Matthaei, Carolina es_CL
Admission datedc.date.accessioned2008-11-10T11:42:23Z
Available datedc.date.available2008-11-10T11:42:23Z
Publication datedc.date.issued2000-11-17
Cita de ítemdc.identifier.citationJOURNAL OF ORGANIC CHEMISTRY 65(23):7949-7958en
Identifierdc.identifier.issn0022-3263
Identifierdc.identifier.urihttp://repositorio.uchile.cl/handle/2250/120553
Abstractdc.description.abstractThe photophysical and photochemical behavior of 1-methyl-3-phenylquinoxalin-2-one (MeNQ) and 3-phenylquinoxalin-2-one (HNQ) in the presence of amines is reported. While HNQ fluorescence shows an auxochromic effect and a bathochromic shift with added amines, explained by association of HNQ with amine in the ground state and emission from both excited species HNQ* and [HNQ-amine]*, both MeNQ and HNQ are photoreduced efficiently on irradiation in the presence of amines, leading to the semireduced quinoxalin-2-ones, MeNQH(-) and HNQH(-), respectively, via an electron-proton-electron transfer, with unit quantum yields at high amine concentrations. The semireduced quinoxalin-2-ones XNQH(-) (X = H, Me) revert almost quantitatively to the parent XNQ in a dark thermal reaction with an activation free energy for MeNQH(-) of 17.4 and 25.9 kcal/mol in acetonitrile and benzene, respectively. Kinetic and spectroscopic (UV and NMR) evidence supports the proposed reaction mechanism for the reversible photoreduction.en
Lenguagedc.language.isoenen
Publisherdc.publisherAMER CHEMICAL SOCen
Keywordsdc.subjectAminesen
Títulodc.titleFormal hydride transfer mechanism for photoreduction of 3-phenylquinoxalin-2-ones by amines. Association of 3-phenylquinoxalin-2-one with aliphatic aminesen
Document typedc.typeArtículo de revistaen


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