Journals / Turkish Journal of Chemistry / 2011 / Cilt: 35 - Sayı: 2

Enantioselective complexation of chiral lariat crown ethers and chiral primary alkylammonium perchlorates

Pages
171–179
DOI
—

Abstract

In order to investigate the enantiomeric recognition abilities toward 2 chiral alkylammonium perchlorates (AmI, AmII) by 1H-NMR titration method in CDCl3, 4 chiral lariat ethers 8-11 with a (p-methoxyphenoxy) methyl flexible side arm were used. The most effective enantiomeric recognition was obtained by LCEs 9 and 11 toward AmII, by KR/KS 6.58 and KS/KR 6.63, respectively. The effect of macroring size, subunit of macroring, and side arm appeared to have strong influence on the binding ability of these alkylammonium ions.

Özet

In order to investigate the enantiomeric recognition abilities toward 2 chiral alkylammonium perchlorates (AmI, AmII) by 1H-NMR titration method in CDCl3, 4 chiral lariat ethers 8-11 with a (p-methoxyphenoxy) methyl flexible side arm were used. The most effective enantiomeric recognition was obtained by LCEs 9 and 11 toward AmII, by KR/KS 6.58 and KS/KR 6.63, respectively. The effect of macroring size, subunit of macroring, and side arm appeared to have strong influence on the binding ability of these alkylammonium ions.

Keywords: Chiral lariat crown ethers, enantioselectivity, complexation properties, molecular recognition, NMR titration