Rationalizing the Regioselectivity of the Diels-Alder Bis-Cycloaddition of Fullerenes

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...

Descripción completa

Detalles Bibliográficos
Autores: García-Rodeja, Yago, Solà i Puig, Miquel, Fenández López, Israel
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/15464
Acceso en línea:http://hdl.handle.net/10256/15464
Access Level:acceso abierto
Palabra clave:Ful·lerens
Diels-Alder, Reacció de
Funcional de densitat, Teoria del
Fullerenes
Diels-Alder reaction
Density functionals
id ES_55ea172a507a45843d51a7bac404bec2
oai_identifier_str oai:recercat.cat:10256/15464
network_acronym_str ES
network_name_str España
repository_id_str
spelling Rationalizing the Regioselectivity of the Diels-Alder Bis-Cycloaddition of FullerenesGarcía-Rodeja, YagoSolà i Puig, MiquelFenández López, IsraelFul·lerensDiels-Alder, Reacció deFuncional de densitat, Teoria delFullerenesDiels-Alder reactionDensity functionalsThe 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 transformationFinancial 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 grantAmerican Chemical Society (ACS)Ministerio de Economía y Competitividad (Espanya)info2018info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionpeer-reviewed9 p.application/pdfhttp://hdl.handle.net/10256/15464http://hdl.handle.net/10256/15464© Journal of Organic Chemistry, 2018, vol. 83, núm. 6, p. 3285-3293Articles publicats (D-Q)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 3293reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.8b00218info:eu-repo/semantics/altIdentifier/issn/0022-3263info:eu-repo/semantics/altIdentifier/eissn/1520-6904info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-85341-PTots els drets reservatsinfo:eu-repo/semantics/openAccessoai:recercat.cat:10256/154642026-05-29T05:05:01Z
dc.title.none.fl_str_mv Rationalizing the Regioselectivity of the Diels-Alder Bis-Cycloaddition of Fullerenes
title Rationalizing the Regioselectivity of the Diels-Alder Bis-Cycloaddition of Fullerenes
spellingShingle Rationalizing the Regioselectivity of the Diels-Alder Bis-Cycloaddition of Fullerenes
García-Rodeja, Yago
Ful·lerens
Diels-Alder, Reacció de
Funcional de densitat, Teoria del
Fullerenes
Diels-Alder reaction
Density functionals
title_short Rationalizing the Regioselectivity of the Diels-Alder Bis-Cycloaddition of Fullerenes
title_full Rationalizing the Regioselectivity of the Diels-Alder Bis-Cycloaddition of Fullerenes
title_fullStr Rationalizing the Regioselectivity of the Diels-Alder Bis-Cycloaddition of Fullerenes
title_full_unstemmed Rationalizing the Regioselectivity of the Diels-Alder Bis-Cycloaddition of Fullerenes
title_sort Rationalizing the Regioselectivity of the Diels-Alder Bis-Cycloaddition of Fullerenes
dc.creator.none.fl_str_mv García-Rodeja, Yago
Solà i Puig, Miquel
Fenández López, Israel
author García-Rodeja, Yago
author_facet García-Rodeja, Yago
Solà i Puig, Miquel
Fenández López, Israel
author_role author
author2 Solà i Puig, Miquel
Fenández López, Israel
author2_role author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (Espanya)
dc.subject.none.fl_str_mv Ful·lerens
Diels-Alder, Reacció de
Funcional de densitat, Teoria del
Fullerenes
Diels-Alder reaction
Density functionals
topic Ful·lerens
Diels-Alder, Reacció de
Funcional de densitat, Teoria del
Fullerenes
Diels-Alder reaction
Density functionals
description 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
publishDate 2018
dc.date.none.fl_str_mv 2018
info
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
peer-reviewed
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/15464
http://hdl.handle.net/10256/15464
url http://hdl.handle.net/10256/15464
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.8b00218
info:eu-repo/semantics/altIdentifier/issn/0022-3263
info:eu-repo/semantics/altIdentifier/eissn/1520-6904
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-85341-P
dc.rights.none.fl_str_mv Tots els drets reservats
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Tots els drets reservats
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 9 p.
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society (ACS)
publisher.none.fl_str_mv American Chemical Society (ACS)
dc.source.none.fl_str_mv © Journal of Organic Chemistry, 2018, vol. 83, núm. 6, p. 3285-3293
Articles publicats (D-Q)
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
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869408341879422976
score 15,812429

Similares en LA Referencia