Rationalizing the Regioselectivity of the Diels-Alder Bis-Cycloaddition of Fullerenes
dc.contributor.author
dc.date.accessioned
2018-05-11T07:04:03Z
dc.date.available
2021-04-07T08:03:00Z
dc.date.issued
2018-03-07
dc.identifier.issn
0022-3263
dc.identifier.uri
dc.description.abstract
The physical factors governing the regioselectivity of the double functionalization of fullerenes have been explored by means of Density Functional Theory calculations. To this end, the second Diels-Alder cycloaddition reactions involving 1,3-butadiene and the parent C60-fullerene as well as the ion-encapsulated system Li+@C60 have been selected. In agreement with previous experimental findings on related processes, it is found that the cycloaddition reaction, involving either C60 or Li+@C60, occurs selectively at specific [6,6]-bonds. The combination of the Activation Strain Model of reactivity and the Energy Decomposition Analysis methods has been applied to gain a quantitative understanding into the markedly different reactivity of the available [6,6]-bonds leading to the observed regioselectivity in the transformation
dc.description.sponsorship
Financial support was provided by the Spanish Ministerio de Economía y Competitividad (MINECO) and FEDER (Grants CTQ2016-78205-P and CTQ2016 81797-REDC to I. F. and CTQ2017-85341-P to M. S.), and Catalan DIUE (projects 2017SGR39, ICREA Academia 2014 prize, and XRQTC to M. S.). The FEDER grant UNGI10-4E-801 has also funded this research. Y. G.-R. acknowledges the MINECO for a FPI grant
dc.format.extent
9 p.
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application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society (ACS)
dc.relation
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-85341-P/ES/AVANCES EN LA REACTIVIDAD DE FULLERENOS Y NANOTUBOS: ESTUDIOS TEORICO-EXPERIMENTALES DE CICLACIONES CATALIZADAS POR METALES DE TRANSICION/
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Versió postprint del document publicat a: https://doi.org/10.1021/acs.joc.8b00218
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© Journal of Organic Chemistry, 2018, vol. 83, núm. 6, p. 3285-3293
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Articles publicats (D-Q)
dc.rights
Tots els drets reservats
dc.source
García-Rodeja, Yago Solà i Puig, Miquel Fenández López, Israel 2018 Rationalizing the Regioselectivity of the Diels-Alder Bis-Cycloaddition of Fullerenes Journal of Organic Chemistry 83 6 3285 3293
dc.subject
dc.title
Rationalizing the Regioselectivity of the Diels-Alder Bis-Cycloaddition of Fullerenes
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/openAccess
dc.embargo.terms
2019-03-07T00:00:00Z
dc.date.embargoEndDate
info:eu-repo/date/embargoEnd/2019-03-07
dc.type.version
info:eu-repo/semantics/acceptedVersion
dc.identifier.doi
dc.identifier.idgrec
028435
dc.contributor.funder
dc.type.peerreviewed
peer-reviewed
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dc.relation.ProjectAcronym
dc.identifier.eissn
1520-6904