DUGiDocsEndohedral metal-induced regioselective formation of bis-prato adduct of Y3N@ Ih-C80 and Gd3N@ Ih-C80
dc.contributor.author
dc.date.accessioned
2015-05-11T09:59:07Z
dc.date.available
2015-05-11T09:59:07Z
dc.date.issued
2015
dc.identifier.issn
0002-7863
dc.identifier.uri
dc.description.abstract
Regioselective bisaddition of M3N@Ih-C80 (M = Y, Gd) was observed for the first time in the Prato reaction with N-ethylglycine and formaldehyde. The main kinetic bisadduct of Y3N@C80 was determined to be a [6,6],[6,6] adduct by 1H and 13C NMR and vis/NIR spectroscopy, and it converted to a mixture of regioisomers upon heating via a sigmatropic rearrangement. The main kinetic bisadduct of Gd3N@C80 (the [6,6],[6,6] adduct on the basis of vis/NIR data) existed stably under thermal conditions without isomerization. The likely position of the second addition of the Gd3N@C80 bisadduct was predicted by DFT calculation
dc.description.sponsorship
This research was supported in part by the Swiss National Foundation (200021-140451 and 200021-156097 to Y.Y.), ETHZ (Grant ETH-25 11-1 to Y.Y.), JST PRESTO (to Y.Y.), the American Heart Association (SDG 0930140N to Y.Y.), the Spanish MECD (Ph.D. Fellowship AP2010-2517 to M.G.-B.), Spanish MINECO (Projects CTQ2011-23156/BQU and CTQ2011-25086/BQU and Juan de la Cierva Postdoctoral Grant JCI-2012-14438 to S.O.), and the European Community (CIG Project PCIG14-GA-2013-630978 to S.O.)
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/
info:eu-repo/grantAgreement/MICINN//CTQ2011-25086/ES/MODELIZACION MULTIESCALAR EN (BIO)QUIMICA/
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Reproducció digital del document publicat a: http://dx.doi.org/10.1021/ja511008z
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© Journal of the American Chemical Society, 2015, vol. 137, núm. 1, p. 58-61
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Articles publicats (D-Q)
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Tots els drets reservats
dc.subject
dc.title
Endohedral metal-induced regioselective formation of bis-prato adduct of Y3N@ Ih-C80 and Gd3N@ Ih-C80
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
dc.type.version
info:eu-repo/semantics/publishedVersion
dc.identifier.doi
dc.identifier.idgrec
023212
dc.contributor.funder
dc.relation.FundingProgramme
dc.relation.ProjectAcronym
dc.identifier.eissn
1520-5126