Synthesis and selective lead(II) binding of achiral and enantiomerically pure chiral acridono-18-crown-6 ether type ligands

Luca Szalay, Viktor Farkas, E. Vass, M. Hollósi, Ildikó Móczár, Áron Pintér, P. Huszthy

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Prompted by the increasing interest in cation complexes of supramolecular host molecules, herein we report the synthesis and CD studies on primary aralkylammonium and metal ion (Na+, K+, Mg2+, Ca2+ and Ag+, Zn2+, Ni2+, Cd 2+, Pb2+) complexes of acridono-18-crown-6 hosts 5, a new family of macrocyclic ligands. CD studies in acetonitrile revealed the selective binding of Pb2+ ions by chiral acridono-18-crown-6 ligands. The CD and corresponding UV spectra show two isosbestic points. The isosbestic points are indicative of a rapid equilibrium of two tautomeric forms, the acridino and hydroxy-acridine, while the other species is the Pb2+ complex. This suggestion is also supported by the change in the FTIR spectra.

Original languageEnglish
Pages (from-to)1487-1493
Number of pages7
JournalTetrahedron Asymmetry
Volume15
Issue number9
DOIs
Publication statusPublished - May 10 2004

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Crown Ethers
Ether
Ethers
ethers
Lead
Ligands
Ions
Acridines
ligands
Fourier Transform Infrared Spectroscopy
synthesis
Acetonitrile
acetonitrile
suggestion
Metal ions
Cations
metal ions
ions
Positive ions
Metals

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Synthesis and selective lead(II) binding of achiral and enantiomerically pure chiral acridono-18-crown-6 ether type ligands. / Szalay, Luca; Farkas, Viktor; Vass, E.; Hollósi, M.; Móczár, Ildikó; Pintér, Áron; Huszthy, P.

In: Tetrahedron Asymmetry, Vol. 15, No. 9, 10.05.2004, p. 1487-1493.

Research output: Contribution to journalArticle

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AU - Vass, E.

AU - Hollósi, M.

AU - Móczár, Ildikó

AU - Pintér, Áron

AU - Huszthy, P.

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AB - Prompted by the increasing interest in cation complexes of supramolecular host molecules, herein we report the synthesis and CD studies on primary aralkylammonium and metal ion (Na+, K+, Mg2+, Ca2+ and Ag+, Zn2+, Ni2+, Cd 2+, Pb2+) complexes of acridono-18-crown-6 hosts 5, a new family of macrocyclic ligands. CD studies in acetonitrile revealed the selective binding of Pb2+ ions by chiral acridono-18-crown-6 ligands. The CD and corresponding UV spectra show two isosbestic points. The isosbestic points are indicative of a rapid equilibrium of two tautomeric forms, the acridino and hydroxy-acridine, while the other species is the Pb2+ complex. This suggestion is also supported by the change in the FTIR spectra.

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