133673-63-9Relevant academic research and scientific papers
Recognition by New Symmetrically Substituted Chiral Diphenyl- and Di-tert-butylpyridino-18-crown-6 and Asymmetrically Substituted Chiral Dimethylpyridino-18-crown-6 Ligands of the Enantiomers of Various Organic Ammonium Perchlorates
Huszthy, Peter,Bradshaw, Jerald S.,Zhu, Cheng Y.,Izatt, Reed M.,Lifson, Shneior
, p. 3330 - 3336 (2007/10/02)
Three new chiral pyridino-18-crown-6 ligands have been prepared.These ligands contain either two phenyl, two tert-butyl, or two methyl substituents on chiral macroring carbon atoms.The chiral di-tert-butyl-substituted diester crown analogue was also prepared.The starting chiral di-tert-butyl-substituted tetraethylene glycol needed to prepare the two di-tert-butyl-substituted crowns was obtained from chiral tert-butyl-1,2-ethanediol, which was resolved from its bis(hydrogen phthalate) brucine salt.A high degree of chiral recognition in CD2Cl2 of the enantiomers of ammonium perchlorate (NapEt) was shown by the diphenyl- and di-tert-butyl-substituted crowns as measured by differences in the free energy of avtivation (ΔGc*) values determined by temperature dependent 1H NMR spectroscopy.The diphenyl- and di-tert-butyl-substituted crowns also exhibited high chiral recognition for the enantiomers of NapEt and other chiral organic ammonium salts in methanol and methanol-chloroform mixtures as shown by a large difference in the log K values determined by a direct 1H NMR technique.
