Synthesis of new diaza-18-crown-6 ethers derived from trans-(R,R)-1,2-diaminocyclohexane and investigation of their enantiomeric discrimination ability with amino acid ester salts

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dc.contributor.authorKarakaplan, Mehmet
dc.contributor.authorAk, Devran
dc.contributor.authorColak, Mehmet
dc.contributor.authorKocakaya, Safak Ozhan
dc.contributor.authorHosgoren, Halil
dc.contributor.authorPirinccioglu, Necmettin
dc.date.accessioned2024-04-24T16:18:26Z
dc.date.available2024-04-24T16:18:26Z
dc.date.issued2013
dc.departmentDicle Üniversitesien_US
dc.description.abstractThe synthesis of four diaza-18-crown-6 ethers with C-2-symmetry derived from trans-(R,R)-1,2-diaminocyclohexane bearing methyl, phenyl and phenoxymethyl moeities attached to a stereogenic centre on the crown ring were achieved. Enantiomeric discrimination of these macrocycles against amino acid methyl ester salts was examined by H-1 NMR titration method. They exhibit strong binding ability and some of them show a very high enantioselectivity towards amino acid esters, corresponding to 537 kJ/mol of binding energy difference in CDCl3 at 25 degrees C. Computational modelling showed parallel results with experimental calculations, thus providing a detailed understanding of molecular recognition mode and binding sites between the hosts and the guests. (C) 2012 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [110T468]en_US
dc.description.sponsorshipThe authors are grateful to the Scientific and Technological Research Council of Turkey (TUBITAK) (No. 110T468) for financial support. We are also grateful to DA Case (University of California, San Francisco) for providing a waiver of AMBER.en_US
dc.identifier.doi10.1016/j.tet.2012.10.020
dc.identifier.endpage358en_US
dc.identifier.issn0040-4020
dc.identifier.issn1464-5416
dc.identifier.issue1en_US
dc.identifier.scopus2-s2.0-84870066638
dc.identifier.scopusqualityQ3
dc.identifier.startpage349en_US
dc.identifier.urihttps://doi.org/10.1016/j.tet.2012.10.020
dc.identifier.urihttps://hdl.handle.net/11468/16088
dc.identifier.volume69en_US
dc.identifier.wosWOS:000313386100045
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofTetrahedron
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectChiral Amino Alcoholsen_US
dc.subjectChiral Diaza Crown Ethersen_US
dc.subjectEnantiomeric Recognitionen_US
dc.subjectAmino Acid Estersen_US
dc.subjectH-1 Nmr Titrationen_US
dc.subjectComputational Modellingen_US
dc.titleSynthesis of new diaza-18-crown-6 ethers derived from trans-(R,R)-1,2-diaminocyclohexane and investigation of their enantiomeric discrimination ability with amino acid ester saltsen_US
dc.titleSynthesis of new diaza-18-crown-6 ethers derived from trans-(R,R)-1,2-diaminocyclohexane and investigation of their enantiomeric discrimination ability with amino acid ester salts
dc.typeArticleen_US

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