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dc.contributor.author | Ríos-Gutiérrez, Mar | - |
dc.contributor.author | Darù, Andrea | - |
dc.contributor.author | Tejero, Tomás | - |
dc.contributor.author | Domingo, Luis R. | - |
dc.contributor.author | Merino, Pedro | - |
dc.date.accessioned | 2017-09-28T09:05:55Z | - |
dc.date.available | 2017-09-28T09:05:55Z | - |
dc.date.issued | 2017 | - |
dc.identifier | doi: 10.1039/C6OB02768G | - |
dc.identifier | issn: 1477-0520 | - |
dc.identifier | e-issn: 1477-0539 | - |
dc.identifier.citation | Organic and Biomolecular Chemistry 15(7): 1618-1627 (2017) | - |
dc.identifier.uri | http://hdl.handle.net/10261/155785 | - |
dc.description.abstract | The [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.sponsorship | This 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.publisher | Royal Society of Chemistry (UK) | - |
dc.relation | info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-76155-R | - |
dc.relation | info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-78669-P | - |
dc.relation.isversionof | Publisher's version | - |
dc.rights | openAccess | - |
dc.title | A molecular electron density theory study of the [3 + 2] cycloaddition reaction of nitrones with ketenes | - |
dc.type | artículo | - |
dc.identifier.doi | 10.1039/C6OB02768G | - |
dc.relation.publisherversion | https://doi.org/10.1039/C6OB02768G | - |
dc.date.updated | 2017-09-28T09:05:55Z | - |
dc.description.version | Peer Reviewed | - |
dc.language.rfc3066 | eng | - |
dc.rights.license | http://creativecommons.org/licenses/by-nc/3.0/ | - |
dc.contributor.funder | Gobierno de Aragón | - |
dc.contributor.funder | European Commission | - |
dc.contributor.funder | Ministerio de Economía y Competitividad (España) | - |
dc.relation.csic | Sí | - |
dc.identifier.funder | http://dx.doi.org/10.13039/501100003329 | es_ES |
dc.identifier.funder | http://dx.doi.org/10.13039/501100000780 | es_ES |
dc.identifier.funder | http://dx.doi.org/10.13039/501100010067 | es_ES |
dc.type.coar | http://purl.org/coar/resource_type/c_6501 | es_ES |
item.fulltext | With Fulltext | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.cerifentitytype | Publications | - |
item.grantfulltext | open | - |
item.openairetype | artículo | - |
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ketenes.pdf | 1,28 MB | Adobe PDF | Visualizar/Abrir |
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