Amino alcohol based chiral solvating agents: synthesis and applications in the NMR enantiodiscrimination of carboxylic acids

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dc.contributor.authorBozkurt, Selahattin
dc.contributor.authorDurmaz, Mustafa
dc.contributor.authorNazıroğlu, Hayriye Nevin
dc.contributor.authorYılmaz, Mustafa
dc.contributor.authorSirit, Abdülkadir
dc.date.accessioned2020-03-26T18:13:43Z
dc.date.available2020-03-26T18:13:43Z
dc.date.issued2011
dc.departmentSelçuk Üniversitesien_US
dc.description.abstractFour optically active amino alcohols were synthesized via the ring opening of (R)-N-(2,3-epoxypropyl)phthalimide with (R)-2-phenyl glycinol, (1R,2S)-cis-1-amino-2-indanol, (R)-2-amino-1-butanol and (S)-phenyl ethylamine in 73-93% yields. The enantioselective recognition of these receptors towards the enantiomers of racemic carboxylic acids was studied by (1)H NMR spectroscopy. The molar ratio and the association constants of the chiral compounds with each of the enantiomers of the guests were determined by using Job plots and a non-linear least-squares fitting method, respectively. Large non-equivalent chemical shifts (up to 30.0 Hz) can be achieved in the presence of chiral amino alcohols 2 and 5. Amongst the chiral receptors used, compound 5 was found to be the best chiral shift reagent, and was effective in the determination of the enantiomeric excess of chiral carboxylic acids. (C) 2011 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipScientific and Technical Research Council of TurkeyTurkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [TUBITAK-109T167]; Research Foundation of Selcuk UniversitySelcuk University [BAP-10101019]en_US
dc.description.sponsorshipWe thank the Scientific and Technical Research Council of Turkey (TUBITAK-109T167) and Research Foundation of Selcuk University (BAP-10101019) for financial support of this work.en_US
dc.identifier.doi10.1016/j.tetasy.2011.02.028en_US
dc.identifier.endpage549en_US
dc.identifier.issn0957-4166en_US
dc.identifier.issue5en_US
dc.identifier.scopusqualityN/Aen_US
dc.identifier.startpage541en_US
dc.identifier.urihttps://dx.doi.org/10.1016/j.tetasy.2011.02.028
dc.identifier.urihttps://hdl.handle.net/20.500.12395/26097
dc.identifier.volume22en_US
dc.identifier.wosWOS:000291139700008en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherPERGAMON-ELSEVIER SCIENCE LTDen_US
dc.relation.ispartofTETRAHEDRON-ASYMMETRYen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.selcuk20240510_oaigen_US
dc.titleAmino alcohol based chiral solvating agents: synthesis and applications in the NMR enantiodiscrimination of carboxylic acidsen_US
dc.typeArticleen_US

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