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dc.contributor.authorFaggi, Enrico
dc.contributor.authorPorcar, Raúl
dc.contributor.authorBolte, Michael
dc.contributor.authorLuis Lafuente, Santiago Vicente
dc.contributor.authorGarcia-Verdugo, Eduardo
dc.contributor.authorAlfonso Rodríguez, Ignacio
dc.date.accessioned2015-07-16T09:42:51Z
dc.date.available2015-07-16T09:42:51Z
dc.date.issued2014-09
dc.identifier.citationFAGGI, Enrico, et al. Chiral Imidazolium Receptors for Citrate and Malate: The Importance of the Preorganization. The Journal of organic chemistry, 2014, 79.19: 9141-9149.ca_CA
dc.identifier.urihttp://hdl.handle.net/10234/127768
dc.description.abstractA family of simple receptors formed by two or three cationic imidazolium arms attached to a central aromatic linkage and displaying different conformational flexibility has been synthesized from the enantiopure (1S,2S)-2-(1-H-imidazol-1-yl)-cyclohexanol. The crystal structures of the corresponding bromides of two of the hosts showed remarkable differences. The tripodal receptor with a trimethylated central benzene ring (1a) showed a cone-type conformation defining an inner anion-binding site, while the bipodal molecule with the central meta-phenylene spacer (m-2a) displayed an extended conformation. The binding properties of the chiral imidazolium hosts toward citrate, isocitrate and the two enantiomers of malate have been studied by 1H NMR titration experiments in 9:1 CD3CN:CD3OH at 298.15 K. Interestingly, 1a showed a stronger interaction with dianionic malate than with the trianionic citrate or isocitrate, suggesting that the smaller guest is better accommodated in the host cavity. Among this family, 1a proved to be the best receptor due to a combination of a larger number of electrostatic and H-bonding interactions and to a more efficient preorganization in the cone-type conformation. This preorganization effect is also present in solution as confirmed by 1H NMR spectroscopy.ca_CA
dc.format.extent8 p.ca_CA
dc.format.mimetypeapplication/pdfca_CA
dc.language.isoengca_CA
dc.publisherAmerican Chemical Societyca_CA
dc.relation.isPartOfJ. Org. Chem., 2014, 79 (19), pp 9141–9149ca_CA
dc.rights© 2014 American Chemical Societyca_CA
dc.subjectCitratesca_CA
dc.subjectAromatic compoundsca_CA
dc.subjectBinding energyca_CA
dc.subjectCrystallographyca_CA
dc.subjectNuclear magnetic resonance spectroscopyca_CA
dc.subjectMalatesca_CA
dc.subjectImidazole derivativeca_CA
dc.titleChiral Imidazolium Receptors for Citrate and Malate: The Importance of the Preorganizationca_CA
dc.typeinfo:eu-repo/semantics/articleca_CA
dc.identifier.doihttp://dx.doi.org/10.1021/jo5014977
dc.rights.accessRightsinfo:eu-repo/semantics/restrictedAccessca_CA
dc.relation.publisherVersionhttp://pubs.acs.org/doi/abs/10.1021/jo5014977ca_CA


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