1597413-22-3Relevant academic research and scientific papers
Synthesis of rigid and C2-symmetric pyridino-15-crown-5 type macrocycles bearing diamide-diester functions: Enantiomeric recognition for chiral primary organoammonium perchlorate salts
?eker, Sevil,Bari?, Deniz,Arslan, Nevin,Turgut, Yilmaz,Pirin??io?lu, Necmettin,To?rul, Mahmut
, p. 411 - 417 (2014/04/17)
Four 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.
