Please use this identifier to cite or link to this item: http://hdl.handle.net/10553/75057
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dc.contributor.authorAzofra Mesa, Luis Miguelen_US
dc.contributor.authorQuesada-Moreno, María Maren_US
dc.contributor.authorAlkorta, Ibonen_US
dc.contributor.authorAvilés-Moreno, Juan Ramónen_US
dc.contributor.authorElguero, Joséen_US
dc.contributor.authorLópez-González, Juan Jesúsen_US
dc.date.accessioned2020-10-28T08:52:11Z-
dc.date.available2020-10-28T08:52:11Z-
dc.date.issued2015en_US
dc.identifier.issn1439-4235en_US
dc.identifier.urihttp://hdl.handle.net/10553/75057-
dc.description.abstractThe biochemically important interconversion process between aldoses and ketoses is assumed to take place via 1,2‐enediol or 1,2‐enediolate intermediates, but such intermediates have never been isolated. The current work was undertaken in an attempt to detect the presence of the 1,2‐enediol structure of glycolaldehyde in alkaline medium, actually a 1,2‐enediolate, and to try to clarify the scarce data existing about both the formation of deprotonated enediol and the aldo‐enediolate equilibrium. The Raman spectra of neutral and basic solutions were recorded as a function of time for eleven days. Several bands associated with the presence of the enediolate were observed in alkaline medium. Glycolaldehyde exists as three different structures in aqueous solution at neutral pH, that is, hydrated aldehydes, aldehydes and dimers, with a respective ratio of approximately 4:0.25:1. Additionally, the formation of Z‐enediolate forms takes place at basic pH, together with an increase in the concentration of aldehyde species, such as 2‐oxoethan‐1‐olate, and a decrease in the concentrations of the hydrated aldehyde and dimeric forms. The theoretical ratio of ≈1.5:1 for aldehyde:Z‐enediolate reproduces the experimental Raman spectrum in basic medium, with an additional contribution of the previously mentioned ratio between the hydrated aldehyde and dimeric forms. Finally, Raman spectroscopy allowed us to monitor the enolization of this carbohydrate model and conclude that aldo‐enediol tautomerism—formally aldo‐enediolate—happens when a suitable amount of basic species is added.en_US
dc.languageengen_US
dc.relation.ispartofChemPhysChemen_US
dc.sourceChemPhysChem [ISSN 1439-4235], v. 16, p. 2226 –2236en_US
dc.subject230226 Bioquímica físicaen_US
dc.subject.otherHydrogen bondsen_US
dc.subject.otherQuantum chemical calculationsen_US
dc.subject.otherRaman spectroscopyen_US
dc.subject.otherSolventsen_US
dc.subject.otherTautomerismen_US
dc.titleUnderstanding the Aldo-Enediolate Tautomerism of Glycolaldehyde in Basic Aqueous Solutionsen_US
dc.typeinfo:eu-repo/semantics/articleen_US
dc.typeArticleen_US
dc.identifier.doi10.1002/cphc.201500139en_US
dc.description.lastpage2236en_US
dc.identifier.issue10-
dc.description.firstpage2226en_US
dc.relation.volume16en_US
dc.investigacionCienciasen_US
dc.type2Artículoen_US
dc.description.numberofpages11en_US
dc.utils.revisionen_US
dc.identifier.ulpgcNoen_US
dc.description.sjr1,334
dc.description.jcr3,138
dc.description.sjrqQ1
dc.description.jcrqQ1
item.grantfulltextnone-
item.fulltextSin texto completo-
crisitem.author.deptFotocatálisis y espectroscopía para aplicaciones medioambientales. Unidad asociada al CSIC a través del Instituto de Ciencias de Materiales de Sevilla-
crisitem.author.deptIU de Estudios Ambientales y Recursos Naturales-
crisitem.author.orcid0000-0003-4974-1670-
crisitem.author.parentorgIU de Estudios Ambientales y Recursos Naturales-
crisitem.author.fullNameAzofra Mesa, Luis Miguel-
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