Şeker, SevilBarış Cebe, DenizArslan, NevinTurgut, YılmazPirinççioğlu, NecmettinToğrul, Mahmut2021-04-092021-04-092014-03-15Şeker, 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.2014.01.0090957-4166https://doi.org/10.1016/j.tetasy.2014.01.009https://hdl.handle.net/20.500.12402/2825Four 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.eninfo:eu-repo/semantics/openAccessAttribution-NonCommercial-ShareAlike 3.0 United StatesArticle255411417N/AQ2