Synthesis of rigid and C2-symmetric 18-crown-6 type macrocycles bearing diamide-diester groups: enantiomeric recognition for ?-(1-naphthyl) ethylammonium perchlorate salts

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dc.contributor.authorBaris, Deniz
dc.contributor.authorSeker, Sevil
dc.contributor.authorHosgoren, Halil
dc.contributor.authorTogrul, Mahmut
dc.date.accessioned2024-04-24T16:18:27Z
dc.date.available2024-04-24T16:18:27Z
dc.date.issued2010
dc.departmentDicle Üniversitesien_US
dc.description.abstractA series of rigid and chiral C-2-symmetric 18-crown-6 type macrocycles (S,S)-4, (S,S)-5, (S,S)-6 and (R,R)-2 bearing diamide-ester groups were synthesized. The binding properties of these macrocycles were examined for ot-(1-naphthypethylammonium perchlorates salts by an 1H NMR titration method. Taking into account the host employed, important differences were observed in the Ka values of (R)- and (S)-enantiomers of guests for macrocycles (S,S)-4 and (S,S)-6, Ks/KR = 3.6, and Ks/KR = 0.1 (KR/Ks = 10.3).6.,6,G= 3.19 and Delta Delta G= -5.77 kJ mol(-1), respectively. The results indicated excellent enantioselectivity of macrocyclic (S,S)-6 towards the enantiomers of alpha-(1-naphthyl)ethylammonium perchlorate salts. (C) 2010 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipScientific and Technical Research Council of Turkey (TUBITAK) [106T395]; Dicle University Research Committee (DUBAP) [06-FF-39, 06-FF-40]en_US
dc.description.sponsorshipThis work was supported by The Scientific and Technical Research Council of Turkey (TUBITAK), under project number: 106T395 and Dicle University Research Committee (DUBAP) under project number 06-FF-39 and 06-FF-40. The authors thank the TUBITAK and DUBAP for supporting this work.en_US
dc.identifier.doi10.1016/j.tetasy.2010.05.051
dc.identifier.endpage1899en_US
dc.identifier.issn0957-4166
dc.identifier.issue15en_US
dc.identifier.scopus2-s2.0-77957563688
dc.identifier.scopusqualityN/A
dc.identifier.startpage1893en_US
dc.identifier.urihttps://doi.org/10.1016/j.tetasy.2010.05.051
dc.identifier.urihttps://hdl.handle.net/11468/16107
dc.identifier.volume21en_US
dc.identifier.wosWOS:000281626300014
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 18-crown-6 type macrocycles bearing diamide-diester groups: enantiomeric recognition for ?-(1-naphthyl) ethylammonium perchlorate saltsen_US
dc.titleSynthesis of rigid and C2-symmetric 18-crown-6 type macrocycles bearing diamide-diester groups: enantiomeric recognition for ?-(1-naphthyl) ethylammonium perchlorate salts
dc.typeArticleen_US

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