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Authordc.contributor.authorAliaga, Christian 
Authordc.contributor.authorCerón-Neculpán, Masiel 
Authordc.contributor.authorSaitz Barría, Claudio 
Authordc.contributor.authorJullian Matthaei, Carolina 
Authordc.contributor.authorSobarzo Sánchez, Eduardo 
Authordc.contributor.authorDe la Fuente, Julio 
Admission datedc.date.accessioned2018-12-20T14:12:54Z
Available datedc.date.available2018-12-20T14:12:54Z
Publication datedc.date.issued2011
Cita de ítemdc.identifier.citationJournal of Photochemistry and Photobiology A: Chemistry, Volumen 222, Issue 2-3, 2018, Pages 360-365
Identifierdc.identifier.issn10106030
Identifierdc.identifier.other10.1016/j.jphotochem.2011.07.011
Identifierdc.identifier.urihttp://repositorio.uchile.cl/handle/2250/154865
Abstractdc.description.abstractDuring the 1H NMR study of the photoreduction of aza-oxoisoaporphines, aza-OIAs, (7H-benzo[e]perimidin-7-ones) by amines we found an unexpected H/D isotopic exchange in the aromatic positions 4 and 6 of these molecules. This surprising exchange motivated us to probe it with previously studied oxoisoaporphines, OIAs, (1-aza-benzo[de]anthracen-7-ones) and 2,3-dihydro-oxoisoaporphines, 2,3-dh-OIAs, (2,3-dihydro-7H-dibenzo[de,h] quinolin-7-ones). All of these compounds photoreduce efficiently in the presence of aliphatic tertiary amines through a stepwise mechanism of electron-proton-electron transfer. This photoreaction generates an AH - anion hydrogenated either at the N-atom, for 2,3-dh-OIAs, or at the O-atom for aza-OIA and OIAs. These long-lived metastable photoproducts revert thermally to the initial oxoisoaporphines nearly quantitatively. In the presence of D2O, regioselective exchange of the aromatic protons at positions 4 and 6 takes place to an extent greater than 90% under very
Lenguagedc.language.isoen
Type of licensedc.rightsAttribution-NonCommercial-NoDerivs 3.0 Chile
Link to Licensedc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/cl/
Sourcedc.sourceJournal of Photochemistry and Photobiology A: Chemistry
Keywordsdc.subjectAzabenzoanthracenones
Keywordsdc.subjectBenzoperimidinones
Keywordsdc.subjectHeterocycle photoreduction
Keywordsdc.subjectIsotopic exchange
Keywordsdc.subjectIsotopic labelling
Keywordsdc.subjectOxoisoaporphines
Títulodc.titleOxoisoaporphines: Regioselective deuterium labelling involving the metastable hydrogenated photoproduct anions
Document typedc.typeArtículo de revista
Catalogueruchile.catalogadorSCOPUS
Indexationuchile.indexArtículo de publicación SCOPUS
uchile.cosechauchile.cosechaSI


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Attribution-NonCommercial-NoDerivs 3.0 Chile
Except where otherwise noted, this item's license is described as Attribution-NonCommercial-NoDerivs 3.0 Chile