Enantiospecific cis-trans isomerization in chiral fulleropyrrolidines: Hydrogen-bonding assistance in the carbanion stabilization in H2O@C60

The stereochemical outcome of cis-trans isomerization of optically pure [60], [70], and endohedral H2O@C60 fulleropyrrolidines reveals that the electronic nature of substituents, fullerene size, and surprisingly the incarcerated water molecule plays a crucial role in this rearrangement process. Theo...

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Detalles Bibliográficos
Autores: Maroto, Enrique E., Mateos, Jaime, Garcia Borràs, Marc, Osuna Oliveras, Sílvia, Filippone, Salvatore, Herranz, María Ángeles, Murata, Yasujiro, Solà i Puig, Miquel, Martín, Nazario
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2015
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:10256/10358
Acceso en línea:http://hdl.handle.net/10256/10358
Access Level:acceso embargado
Palabra clave:Ful·lerens
Fullerenes
Isomerització
Isomerization
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spelling Enantiospecific cis-trans isomerization in chiral fulleropyrrolidines: Hydrogen-bonding assistance in the carbanion stabilization in H2O@C60Maroto, Enrique E.Mateos, JaimeGarcia Borràs, MarcOsuna Oliveras, SílviaFilippone, SalvatoreHerranz, María ÁngelesMurata, YasujiroSolà i Puig, MiquelMartín, NazarioFul·lerensFullerenesIsomeritzacióIsomerizationThe stereochemical outcome of cis-trans isomerization of optically pure [60], [70], and endohedral H2O@C60 fulleropyrrolidines reveals that the electronic nature of substituents, fullerene size, and surprisingly the incarcerated water molecule plays a crucial role in this rearrangement process. Theoretical DFT calculations are in very good agreement with the experimental fi ndings. On the basis of the experimental results and computational calculations, a plausible reaction mechanism involving the hydrogen-bonding assistance of the inner water molecule in the carbanion stabilization of endofullerene is proposedFinancial support by the European Research Council (ERC-320441-Chirallcarbon and FP7-PEOPLE-2013-CIG-630978 to S.O.), the Ministerio de Economia y Competitividad (MINECO) of Spain (projects CTQ2011-24652/BQU and CTQ2011-23156/BQU, JdlC contract to S.O, and AP2010-2517 to M.G.-B.), the CAM (PHOTOCARBON project S2013/MIT-2841), the Generalitat de Catalunya (project number 2014SGR931 and ICREA Academia 2009 to M.S.) is acknowledged. N.M. thanks to the Alexander von Humboldt FoundationAmerican Chemical Society (ACS)Ministerio de Ciencia e Innovación (Espanya)Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recercainfoinfo2015info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10256/10358http://hdl.handle.net/10256/10358© Journal of the American Chemical Society, 2015, vol. 137, núm. 3, p. 1190-1197Articles publicats (D-Q)reponame: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/ja5108854info:eu-repo/semantics/altIdentifier/issn/0002-7863info:eu-repo/semantics/altIdentifier/eissn/1520-5126info:eu-repo/grantAgreement/MICINN//CTQ2011-23156AGAUR/2014-2016/2014 SGR-931info:eu-repo/grantAgreement/EC/FP7/630978info:eu-repo/grantAgreement/EC/FP7/320441Tots els drets reservatsinfo:eu-repo/semantics/embargoedAccessoai:recercat.cat:10256/103582026-05-29T05:05:01Z
dc.title.none.fl_str_mv Enantiospecific cis-trans isomerization in chiral fulleropyrrolidines: Hydrogen-bonding assistance in the carbanion stabilization in H2O@C60
title Enantiospecific cis-trans isomerization in chiral fulleropyrrolidines: Hydrogen-bonding assistance in the carbanion stabilization in H2O@C60
spellingShingle Enantiospecific cis-trans isomerization in chiral fulleropyrrolidines: Hydrogen-bonding assistance in the carbanion stabilization in H2O@C60
Maroto, Enrique E.
Ful·lerens
Fullerenes
Isomerització
Isomerization
title_short Enantiospecific cis-trans isomerization in chiral fulleropyrrolidines: Hydrogen-bonding assistance in the carbanion stabilization in H2O@C60
title_full Enantiospecific cis-trans isomerization in chiral fulleropyrrolidines: Hydrogen-bonding assistance in the carbanion stabilization in H2O@C60
title_fullStr Enantiospecific cis-trans isomerization in chiral fulleropyrrolidines: Hydrogen-bonding assistance in the carbanion stabilization in H2O@C60
title_full_unstemmed Enantiospecific cis-trans isomerization in chiral fulleropyrrolidines: Hydrogen-bonding assistance in the carbanion stabilization in H2O@C60
title_sort Enantiospecific cis-trans isomerization in chiral fulleropyrrolidines: Hydrogen-bonding assistance in the carbanion stabilization in H2O@C60
dc.creator.none.fl_str_mv Maroto, Enrique E.
Mateos, Jaime
Garcia Borràs, Marc
Osuna Oliveras, Sílvia
Filippone, Salvatore
Herranz, María Ángeles
Murata, Yasujiro
Solà i Puig, Miquel
Martín, Nazario
author Maroto, Enrique E.
author_facet Maroto, Enrique E.
Mateos, Jaime
Garcia Borràs, Marc
Osuna Oliveras, Sílvia
Filippone, Salvatore
Herranz, María Ángeles
Murata, Yasujiro
Solà i Puig, Miquel
Martín, Nazario
author_role author
author2 Mateos, Jaime
Garcia Borràs, Marc
Osuna Oliveras, Sílvia
Filippone, Salvatore
Herranz, María Ángeles
Murata, Yasujiro
Solà i Puig, Miquel
Martín, Nazario
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación (Espanya)
Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recerca
dc.subject.none.fl_str_mv Ful·lerens
Fullerenes
Isomerització
Isomerization
topic Ful·lerens
Fullerenes
Isomerització
Isomerization
description The stereochemical outcome of cis-trans isomerization of optically pure [60], [70], and endohedral H2O@C60 fulleropyrrolidines reveals that the electronic nature of substituents, fullerene size, and surprisingly the incarcerated water molecule plays a crucial role in this rearrangement process. Theoretical DFT calculations are in very good agreement with the experimental fi ndings. On the basis of the experimental results and computational calculations, a plausible reaction mechanism involving the hydrogen-bonding assistance of the inner water molecule in the carbanion stabilization of endofullerene is proposed
publishDate 2015
dc.date.none.fl_str_mv 2015
info
info
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/10358
http://hdl.handle.net/10256/10358
url http://hdl.handle.net/10256/10358
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/ja5108854
info:eu-repo/semantics/altIdentifier/issn/0002-7863
info:eu-repo/semantics/altIdentifier/eissn/1520-5126
info:eu-repo/grantAgreement/MICINN//CTQ2011-23156
AGAUR/2014-2016/2014 SGR-931
info:eu-repo/grantAgreement/EC/FP7/630978
info:eu-repo/grantAgreement/EC/FP7/320441
dc.rights.none.fl_str_mv Tots els drets reservats
info:eu-repo/semantics/embargoedAccess
rights_invalid_str_mv Tots els drets reservats
eu_rights_str_mv embargoedAccess
dc.format.none.fl_str_mv 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 the American Chemical Society, 2015, vol. 137, núm. 3, p. 1190-1197
Articles publicats (D-Q)
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
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score 15.811543

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