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Enantiospecific cis−trans Isomerization in Chiral Fulleropyrrolidines:Hydrogen-Bonding Assistance in the Carbanion Stabilization in H2O@C60

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dc.contributor.authorMaroto, Enrique
dc.contributor.authorMateos, Jaime
dc.contributor.authorGarcía Borràs, Marc
dc.contributor.authorOsuna, Silvia
dc.contributor.authorFilippone, Salvatore
dc.contributor.authorHerranz, M.Angeles
dc.contributor.authorMurata, Yasujiro
dc.contributor.authorSolà, Miquel
dc.contributor.authorMartín, Nazario
dc.date.accessioned2023-06-19T14:59:45Z
dc.date.available2023-06-19T14:59:45Z
dc.date.issued2015-01
dc.description.abstractThe 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 findings. 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.departmentDepto. de Química Orgánica
dc.description.facultyFac. de Ciencias Químicas
dc.description.refereedTRUE
dc.description.sponsorshipUnión Europea. FP7
dc.description.sponsorshipEuropean Research Council
dc.description.sponsorshipComunidad de Madrid
dc.description.sponsorshipMinisterio de Economía y Competitividad (MINECO)
dc.description.sponsorshipGeneralitat de Catalunya
dc.description.statuspub
dc.eprint.idhttps://eprints.ucm.es/id/eprint/35970
dc.identifier.doi10.1021/ja5108854
dc.identifier.issn1520-5126
dc.identifier.officialurlhttp://pubs.acs.org/doi/pdf/10.1021/ja5108854
dc.identifier.urihttps://hdl.handle.net/20.500.14352/35074
dc.issue.number3
dc.journal.titleJournal of the American Chemical Society
dc.language.isoeng
dc.page.final1197
dc.page.initial1190
dc.publisherACS
dc.relation.projectIDCHIRALLCARBON (320441) FP7-PEOPLE-2013-CIG-630978
dc.relation.projectIDFP7-PEOPLE-2013-CIG-630978
dc.relation.projectIDPHOTOCARBON (S2013/MIT-2841)
dc.relation.projectIDMADRIDSOLAR-2 (S2009/PPQ-1533)
dc.relation.projectIDCTQ2011-24652/BQU
dc.relation.projectIDCTQ2011-23156/BQU
dc.relation.projectIDproject number 2014SGR931 and ICREA Academia 2009 to M.S
dc.relation.projectIDAP2010- 2517 to M.G.-B.
dc.rights.accessRightsopen access
dc.subject.cdu547
dc.subject.keywordHydrogen
dc.subject.keywordHydrogen bonds
dc.subject.keywordIsomers
dc.subject.keywordMolecules
dc.subject.keywordStabilization
dc.subject.keywordStereochemistry Cis-trans Isomerization
dc.subject.keywordComputational calculations
dc.subject.keywordDFT calculation
dc.subject.keywordElectronic natures
dc.subject.keywordEndo-fullerenes
dc.subject.keywordFulleropyrrolidines
dc.subject.keywordReaction mechanism
dc.subject.keywordRearrangement process
dc.subject.ucmQuímica orgánica (Química)
dc.subject.unesco2306 Química Orgánica
dc.titleEnantiospecific cis−trans Isomerization in Chiral Fulleropyrrolidines:Hydrogen-Bonding Assistance in the Carbanion Stabilization in H2O@C60
dc.typejournal article
dc.volume.number137
dspace.entity.typePublication
relation.isAuthorOfPublicationb89322ba-6e32-46b6-9008-9d8ac017f23e
relation.isAuthorOfPublication.latestForDiscoveryb89322ba-6e32-46b6-9008-9d8ac017f23e

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