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Vibrational circular dichroism (VCD) methodology for the measurement of enantiomeric excess in chiral compounds in solid phase and for the complementary use of NMR and VCD techniques in solution: the camphor case

dc.contributor.authorQuesada-Moreno, María del Mar
dc.contributor.authorVirgili, Albert
dc.contributor.authorMonteagudo, Eva
dc.contributor.authorClaramunt, Rosa M.
dc.contributor.authorAvilés-Moreno, Juan Ramón
dc.contributor.authorLópez-González, Juan Jesús
dc.contributor.authorAlkorta, Ibon
dc.contributor.authorElguero, José
dc.date.accessioned2025-01-30T07:24:53Z
dc.date.available2025-01-30T07:24:53Z
dc.date.issued2018
dc.description.abstractFor the first time, the success of a methodology for the determination of enantiomeric excesses (% ee) in chiral solid samples by vibrational circular dichroism (VCD) spectroscopy is reported. We have used camphor to determine the % ee in a blind sample constituted by a mixture of its two enantiomers as a test of the validity of our approach. IR and VCD spectra of different enantiomeric mixtures of R/S-camphor in nujol mulls were recorded and linear regressions of VCD intensities (ΔAbs.) vs. % ee for selected bands were found. Finally, the VCD intensities of a blind sample were interpolated in these linear regressions, obtaining its % ee with a rms of 2.4. These results in the solid phase were complemented with the determination of % ee in the liquid phase by VCD and NMR techniques, which are proved to be complementary techniques to carry out this kind of analysis. In the same way as in the VCD solid phase, linear regressions of ΔAbs. vs. % ee for selected bands were established, obtaining a rms of 1.1 in the % ee determination of a blind sample. 1H NMR experiments at 600 MHz using the chiral solvating agent, (S,S)-ABTE, allow to determine in CD2Cl2 solution the proportions of enantiomers with great accuracy. 13C CPMAS NMR spectra prove that this technique cannot be used for conglomerates and/or solid solutions.es_ES
dc.description.sponsorshipThis work was carried out with financial support from the Ministerio de Economía y Competitividad (Project Nos. CTQ2012-32436, CTQ2014-56833-R and CTQ2015-63997-C2-2-P), CICE/JA-FEDER-UJA:Plan de Fortalecimiento de las Capacidades de I+D+i/2014-15 (UJA2013/08/03) and Comunidad Autónoma de Madrid (Project FOTOCARBON, ref. S2013/MIT-2841). Authors thank the University of Jaén for continuing financial support, for bridge projects (UJA2015/08/07 and UJA2016/08/15), for Acción 2: Financiación de Incentivos a la Excelencia de I+D+i de la UJA 2014-15 in 2014 and 2015 calls and to its CICT for instrumental facilities. M.M.Q.M. thanks the University of Jaén for both a pre- and a post-doctoral fellowships. We also thank the Servei de Ressonància Magnètica Nuclear, Universitat Autònoma de Barcelona, for allocating instrument time to this project.es_ES
dc.identifier.citationAnalyst, 2018,143, 1406-1416es_ES
dc.identifier.issn1364-5528es_ES
dc.identifier.other10.1039/C7AN01855Jes_ES
dc.identifier.urihttps://hdl.handle.net/10953/4565
dc.language.isoenges_ES
dc.publisherRoyal Society of Chemistryes_ES
dc.relation.ispartofAnalystes_ES
dc.rightsAtribución-NoComercial-SinDerivadas 3.0 España*
dc.rights.accessRightsinfo:eu-repo/semantics/openAccesses_ES
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/es/*
dc.subjectVibrational circular dichroismes_ES
dc.subjectCamphores_ES
dc.subjectSolid statees_ES
dc.subjectEnantiomeric excesses_ES
dc.subjectNMRes_ES
dc.titleVibrational circular dichroism (VCD) methodology for the measurement of enantiomeric excess in chiral compounds in solid phase and for the complementary use of NMR and VCD techniques in solution: the camphor casees_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.type.versioninfo:eu-repo/semantics/draftes_ES

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