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dc.contributor.authorRíos-Gutiérrez, Mar-
dc.contributor.authorDarù, Andrea-
dc.contributor.authorTejero, Tomás-
dc.contributor.authorDomingo, Luis R.-
dc.contributor.authorMerino, Pedro-
dc.date.accessioned2017-09-28T09:05:55Z-
dc.date.available2017-09-28T09:05:55Z-
dc.date.issued2017-
dc.identifierdoi: 10.1039/C6OB02768G-
dc.identifierissn: 1477-0520-
dc.identifiere-issn: 1477-0539-
dc.identifier.citationOrganic and Biomolecular Chemistry 15(7): 1618-1627 (2017)-
dc.identifier.urihttp://hdl.handle.net/10261/155785-
dc.description.abstractThe [3 + 2] cycloaddition (32CA) reaction between nitrones and ketenes has been studied within the Molecular Electron Density Theory (MEDT) at the Density Functional Theory (DFT) MPWB1K/6-311G(d,p) computational level. Analysis of the conceptual DFT reactivity indices allows the explanation of the reactivity, and the chemo- and regioselectivity experimentally observed. The particular mechanism of this 32CA reaction involving low electrophilic ketenes has been elucidated by using a bonding evolution theory (BET) study. It is determined that this reaction takes place in one kinetic step only but in a non-concerted manner since two stages are clearly identified. Indeed, the formation of the second C-O bond begins when the first O-C bond is already formed. This study has also been applied to predict the reactivity of nitrones with highly electrophilic ketenes. Interestingly, this study predicts a switch to a two-step mechanism due to the higher polar character of this zw-type 32CA reaction. In both cases, BET supports the non-concerted nature of the 32CA reactions between nitrones and ketenes.-
dc.description.sponsorshipThis research was supported by the Spanish MINECO (FEDER CTQ2016-78669-P and CTQ2016-76155-R), and the Government of Aragón (Grupos Consolidados, E.10). M. R.-G. thanks MINECO for a pre-doctoral contract co-financed by the European Social Fund (BES-2014-068258).-
dc.publisherRoyal Society of Chemistry (UK)-
dc.relationMINECO/ICTI2013-2016/CTQ2016-76155-R-
dc.relationMINECO/ICTI2013-2016/CTQ2016-78669-P-
dc.relation.isversionofPublisher's version-
dc.rightsopenAccess-
dc.titleA molecular electron density theory study of the [3 + 2] cycloaddition reaction of nitrones with ketenes-
dc.typeartículo-
dc.identifier.doihttp://dx.doi.org/10.1039/C6OB02768G-
dc.relation.publisherversionhttps://doi.org/10.1039/C6OB02768G-
dc.date.updated2017-09-28T09:05:55Z-
dc.description.versionPeer Reviewed-
dc.language.rfc3066eng-
dc.rights.licensehttp://creativecommons.org/licenses/by-nc/3.0/-
dc.contributor.funderGobierno de Aragón-
dc.contributor.funderEuropean Commission-
dc.contributor.funderMinisterio de Economía y Competitividad (España)-
dc.relation.csic-
dc.identifier.funderhttp://dx.doi.org/10.13039/501100003329es_ES
dc.identifier.funderhttp://dx.doi.org/10.13039/501100000780es_ES
dc.identifier.funderhttp://dx.doi.org/10.13039/501100010067es_ES
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