Synthesis of rigid and C2-symmetric pyridino-15-crown-5 type macrocycles bearing diamide-diester functions: enantiomeric recognition for chiral primary organoammonium perchlorate salts

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dc.contributor.authorSeker, Sevil
dc.contributor.authorBaris, Deniz
dc.contributor.authorArslan, Nevin
dc.contributor.authorTurgut, Yilmaz
dc.contributor.authorPirinccioglu, Necmettin
dc.contributor.authorTogrul, Mahmut
dc.date.accessioned2024-04-24T16:18:27Z
dc.date.available2024-04-24T16:18:27Z
dc.date.issued2014
dc.departmentDicle Üniversitesien_US
dc.description.abstractFour novel C-2-symmetric macrocyclic compounds with a pyridine function and possessing amide and ester lingeages were prepared. The enantiomeric discrimination abilities of these macrocycles against alpha-phenylethylammonium and alpha-(1-naphthyl)ethylammonium perchlorate salts were measured by standard H-1 NMR titration techniques in DMSO-d(6). A binding constant ratio of 31 (Kbind(S)/Kbind(R)) for two enantiomers of alpha-(1-naphthyl)ethylammonium salt with the macrocyclic host (S,S)-4 bearing phenyl arms was observed, which corresponds to an enantiomeric discrimination of approximately 94%. Molecular dynamic calculations were performed for some of the supramolecular complexes to in order to gain insight into the mode of molecular recognition between the macrocyclic compounds and ammonium salts; these results were consistent with experimental observations, which may be relevant to those in biochemical processes occurring in organisms. (C) 2014 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipScientific and Technical Research Council of Turkey (TUBITAK) [106T395]; Dicle University Research Council (DUBAP) [10-FF-10, 10-FF-11]en_US
dc.description.sponsorshipWe are grateful to the Scientific and Technical Research Council of Turkey (TUBITAK) for supporting the project (106T395) and Dicle University Research Council (DUBAP) for supporting the projects (10-FF-10 and 10-FF-11). 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.tetasy.2014.01.009
dc.identifier.endpage417en_US
dc.identifier.issn0957-4166
dc.identifier.issue5en_US
dc.identifier.scopus2-s2.0-84897132801
dc.identifier.scopusqualityN/A
dc.identifier.startpage411en_US
dc.identifier.urihttps://doi.org/10.1016/j.tetasy.2014.01.009
dc.identifier.urihttps://hdl.handle.net/11468/16111
dc.identifier.volume25en_US
dc.identifier.wosWOS:000334985000003
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofTetrahedron-Asymmetry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject[No Keyword]en_US
dc.titleSynthesis of rigid and C2-symmetric pyridino-15-crown-5 type macrocycles bearing diamide-diester functions: enantiomeric recognition for chiral primary organoammonium perchlorate saltsen_US
dc.titleSynthesis of rigid and C2-symmetric pyridino-15-crown-5 type macrocycles bearing diamide-diester functions: enantiomeric recognition for chiral primary organoammonium perchlorate salts
dc.typeArticleen_US

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