Synthesis of rigid and C2-symmetric 18-crown-6 type macrocycles bearing diamide-diester groups: enantiomeric recognition for ?-(1-naphthyl) ethylammonium perchlorate salts
dc.contributor.author | Baris, Deniz | |
dc.contributor.author | Seker, Sevil | |
dc.contributor.author | Hosgoren, Halil | |
dc.contributor.author | Togrul, Mahmut | |
dc.date.accessioned | 2024-04-24T16:18:27Z | |
dc.date.available | 2024-04-24T16:18:27Z | |
dc.date.issued | 2010 | |
dc.department | Dicle Üniversitesi | en_US |
dc.description.abstract | A 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.sponsorship | Scientific and Technical Research Council of Turkey (TUBITAK) [106T395]; Dicle University Research Committee (DUBAP) [06-FF-39, 06-FF-40] | en_US |
dc.description.sponsorship | This 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.doi | 10.1016/j.tetasy.2010.05.051 | |
dc.identifier.endpage | 1899 | en_US |
dc.identifier.issn | 0957-4166 | |
dc.identifier.issue | 15 | en_US |
dc.identifier.scopus | 2-s2.0-77957563688 | |
dc.identifier.scopusquality | N/A | |
dc.identifier.startpage | 1893 | en_US |
dc.identifier.uri | https://doi.org/10.1016/j.tetasy.2010.05.051 | |
dc.identifier.uri | https://hdl.handle.net/11468/16107 | |
dc.identifier.volume | 21 | en_US |
dc.identifier.wos | WOS:000281626300014 | |
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 18-crown-6 type macrocycles bearing diamide-diester groups: enantiomeric recognition for ?-(1-naphthyl) ethylammonium perchlorate salts | en_US |
dc.title | Synthesis of rigid and C2-symmetric 18-crown-6 type macrocycles bearing diamide-diester groups: enantiomeric recognition for ?-(1-naphthyl) ethylammonium perchlorate salts | |
dc.type | Article | en_US |