Synthesis and pKa determination of new enantiopure dimethyl-substituted acridino-crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies

Tamás Németh, Gergő Dargó, József Levente Petró, Zsófia Petrik, Sándor Lévai, Balázs Krámos, Zoltán Béni, József Nagy, György Tibor Balogh, P. Huszthy, Tünde Tóth

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3 Citations (Scopus)


New enantiopure dimethyl-substituted acridino-18-crown-6 and acridino-21-crown-7 ethers containing a carboxyl group at position 9 of the acridine ring [(S,S)-8, (S,S)-9, (R,R)-10] were synthesized. The pKa values of the new crown ethers [(S,S)-8, (S,S)-9, (R,R)-10] and of an earlier reported macrocycle [(R,R)-2] were determined by UV-pH titrations. Crown ether (S,S)-8 was attached to silica gel by covalent bonds and the enantiomeric separation ability of the newly prepared chiral stationary phase [(S,S)-CSP-12] was studied by high-performance liquid chromatography (HPLC). Homochiral preference was observed and the best separation was achieved for the enantiomers of 1-NEA. Ligands (S,S)-9 and (R,R)-10 are precursors of enantioselective sensor and selector molecules for the enantiomers of protonated primary amines, amino acids, and their derivatives.

Original languageEnglish
Pages (from-to)522-535
Number of pages14
Issue number9
Publication statusPublished - Jan 1 2017



  • acridino-crown ethers
  • chiral stationary phase
  • enantiomeric recognition
  • HPLC
  • pK determination
  • zwitterionic form

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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