Synthesis of new optically active acridino-18-crown-6 ligands and studies of their potentiometric selectivity toward the enantiomers of protonated 1-phenylethylamine and metal ions

Júlia Kertész, Péter Huszthy, Attila Kormos, Ferenc Bertha, Viola Horváth, George Horvai

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15 Citations (Scopus)

Abstract

Starting from commercially available and relatively inexpensive chemicals, new enantiopure diisobutyl- and dioctyl-substituted acridino-18-crown-6 ether-type ligands [(R,R)-3] and [(R,R)-4], respectively were prepared. The two lipophilic isobutyl [(R,R)-3] and octyl [(R,R)-4] groups on the stereogenic centers of these macrocycles made it possible to use them as potentiometric sensor molecules when incorporated into plasticized PVC membrane electrodes. Ligand (R,R)-3 showed appreciable enantioselectivity toward the enantiomers of 1-phenylethylammonium chloride while macrocycle (R,R)-4 exhibited a high selectivity toward the silver ion.

Original languageEnglish
Pages (from-to)2795-2801
Number of pages7
JournalTetrahedron Asymmetry
Volume20
Issue number24
DOIs
Publication statusPublished - Dec 22 2009

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ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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