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.authorid0000-0001-5860-2133en_US
dc.authorid0000-0003-0142-9215en_US
dc.authorid0000-0001-9805-9745en_US
dc.contributor.authorŞeker, Sevil
dc.contributor.authorBarış Cebe, Deniz
dc.contributor.authorArslan, Nevin
dc.contributor.authorTurgut, Yılmaz
dc.contributor.authorPirinççioğlu, Necmettin
dc.contributor.authorToğrul, Mahmut
dc.date.accessioned2021-04-09T07:15:05Z
dc.date.available2021-04-09T07:15:05Z
dc.date.issued2014-03-15en_US
dc.departmentBatman Üniversitesi Fen - Edebiyat Fakültesi Kimya Bölümüen_US
dc.description.abstractFour novel C2-symmetric macrocyclic compounds with a pyridine function and possessing amide and ester lingeages were prepared. The enantiomeric discrimination abilities of these macrocycles against α-phenylethylammonium and α-(1-naphthyl)ethylammonium perchlorate salts were measured by standard 1H NMR titration techniques in DMSO-d6. A binding constant ratio of 31 (Kbind(S)/Kbind(R)) for two enantiomers of α-(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.en_US
dc.identifier.citationŞeker, S., Barış Cebe, D., Arslan, N., Turgut, Y., Pirinççioğlu, N., Toğrul, M. (2014). Synthesis of rigid and C2-symmetric pyridino-15-crown-5 type macrocycles bearing diamide–diester functions: enantiomeric recognition for chiral primary organoammonium perchlorate salts. Tetrahedron: Asymmetry, 25 (5), pp. 411-417. https://doi.org/10.1016/j.tetasy.2014.01.009en_US
dc.identifier.endpage417en_US
dc.identifier.issn0957-4166
dc.identifier.issue5en_US
dc.identifier.scopusqualityN/Aen_US
dc.identifier.startpage411en_US
dc.identifier.urihttps://doi.org/10.1016/j.tetasy.2014.01.009
dc.identifier.urihttps://hdl.handle.net/20.500.12402/2825
dc.identifier.volume25en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.relation.isversionof10.1016/j.tetasy.2014.01.009en_US
dc.relation.journalTetrahedron: Asymmetryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.rightsAttribution-NonCommercial-ShareAlike 3.0 United States*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/3.0/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.typeArticleen_US

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