Synthesis of rigid and C2-symmetric pyridino-15-crown-5 type macrocycles bearing diamide-diester functions: enantiomeric recognition for chiral primary organoammonium perchlorate salts
dc.contributor.author | Seker, Sevil | |
dc.contributor.author | Baris, Deniz | |
dc.contributor.author | Arslan, Nevin | |
dc.contributor.author | Turgut, Yilmaz | |
dc.contributor.author | Pirinccioglu, Necmettin | |
dc.contributor.author | Togrul, Mahmut | |
dc.date.accessioned | 2024-04-24T16:18:27Z | |
dc.date.available | 2024-04-24T16:18:27Z | |
dc.date.issued | 2014 | |
dc.department | Dicle Üniversitesi | en_US |
dc.description.abstract | Four 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.sponsorship | Scientific and Technical Research Council of Turkey (TUBITAK) [106T395]; Dicle University Research Council (DUBAP) [10-FF-10, 10-FF-11] | en_US |
dc.description.sponsorship | We 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.doi | 10.1016/j.tetasy.2014.01.009 | |
dc.identifier.endpage | 417 | en_US |
dc.identifier.issn | 0957-4166 | |
dc.identifier.issue | 5 | en_US |
dc.identifier.scopus | 2-s2.0-84897132801 | |
dc.identifier.scopusquality | N/A | |
dc.identifier.startpage | 411 | en_US |
dc.identifier.uri | https://doi.org/10.1016/j.tetasy.2014.01.009 | |
dc.identifier.uri | https://hdl.handle.net/11468/16111 | |
dc.identifier.volume | 25 | en_US |
dc.identifier.wos | WOS:000334985000003 | |
dc.identifier.wosquality | Q2 | |
dc.indekslendigikaynak | Web of Science | |
dc.indekslendigikaynak | Scopus | |
dc.language.iso | en | en_US |
dc.publisher | Pergamon-Elsevier Science Ltd | en_US |
dc.relation.ispartof | Tetrahedron-Asymmetry | |
dc.relation.publicationcategory | Makale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı | en_US |
dc.rights | info:eu-repo/semantics/closedAccess | en_US |
dc.subject | [No Keyword] | en_US |
dc.title | Synthesis of rigid and C2-symmetric pyridino-15-crown-5 type macrocycles bearing diamide-diester functions: enantiomeric recognition for chiral primary organoammonium perchlorate salts | en_US |
dc.title | Synthesis of rigid and C2-symmetric pyridino-15-crown-5 type macrocycles bearing diamide-diester functions: enantiomeric recognition for chiral primary organoammonium perchlorate salts | |
dc.type | Article | en_US |