DUGiDocsEnantiospecific cis-trans isomerization in chiral fulleropyrrolidines: Hydrogen-bonding assistance in the carbanion stabilization in H2O@C60
dc.contributor.author
dc.date.accessioned
2015-05-11T09:45:05Z
dc.date.available
2015-05-11T09:45:05Z
dc.date.issued
2015
dc.identifier.issn
0002-7863
dc.identifier.uri
dc.description.abstract
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
dc.description.sponsorship
Financial 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 Foundation
dc.format.mimetype
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society (ACS)
dc.relation
info:eu-repo/grantAgreement/MICINN//CTQ2011-23156/ES/AVANCES EN CATALISIS Y AROMATICIDAD/
AGAUR/2014-2016/2014 SGR-931
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Reproducció digital del document publicat a: http://dx.doi.org/10.1021/ja5108854
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© Journal of the American Chemical Society, 2015, vol. 137, núm. 3, p. 1190-1197
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Articles publicats (D-Q)
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Tots els drets reservats
dc.subject
dc.title
Enantiospecific cis-trans isomerization in chiral fulleropyrrolidines: Hydrogen-bonding assistance in the carbanion stabilization in H2O@C60
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/embargoedAccess
dc.embargo.terms
Cap
dc.date.embargoEndDate
info:eu-repo/date/embargoEnd/2026-01-01
dc.relation.projectID
info:eu-repo/grantAgreement/EC/FP7/630978/EU/Computational Exploration of Directed Evolution rules for tuning enzymatic activities/DIREVENZYME
info:eu-repo/grantAgreement/EC/FP7/320441/EU/Chiral Allotropes of Carbon/CHIRALLCARBON
dc.type.version
info:eu-repo/semantics/publishedVersion
dc.identifier.doi
dc.identifier.idgrec
023190
dc.contributor.funder
dc.relation.ProjectAcronym
dc.identifier.eissn
1520-5126