Pyrimidino-and proton-ionizable pyrimidono-crown ether ligands

Synthesis and preliminary complexation studies

J. Ty Redd, Jerald S. Bradshaw, P. Huszthy, Reed M. Izatt

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Pyrimidino-crown ethers were prepared in 30-50% yields by reacting the ditosylate derivative of the appropriate oligoethylene glycol with 4-methoxy-5-methyl-2,6-pyrimidinedimethanol under basic conditions. A new macrocyclic ligand containing a proton-ionizable pyrimidone subcyclic unit was prepared in 88% yield by treating the appropriate pyrimidino-crown ether with 5 M NaOH in 50% (v/v) aqueous methanol. Preliminary complexation properties of some of these new compounds were studied using various NMR spectral techniques. Good enantiomeric recognition was exhibited by a chiral pyrimidino-crown ether for the enantiomers of 1-(α-naphthyl)ethylammonium perchlorate.

Original languageEnglish
Pages (from-to)301-308
Number of pages8
JournalJournal of Inclusion Phenomena and Molecular Recognition in Chemistry
Volume29
Issue number3-4
Publication statusPublished - Nov 1997

Fingerprint

Crown Ethers
Complexation
protons
Protons
ethers
Ligands
ligands
synthesis
Pyrimidinones
perchlorates
glycols
Glycols
Enantiomers
enantiomers
Methanol
methanol
methyl alcohol
chemical derivatives
Nuclear magnetic resonance
Derivatives

Keywords

  • Benzylammonium complexes
  • Crown ether
  • Pyrimidine-containing crown ether
  • Pyrimidone-containing crown ether

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics

Cite this

Pyrimidino-and proton-ionizable pyrimidono-crown ether ligands : Synthesis and preliminary complexation studies. / Redd, J. Ty; Bradshaw, Jerald S.; Huszthy, P.; Izatt, Reed M.

In: Journal of Inclusion Phenomena and Molecular Recognition in Chemistry, Vol. 29, No. 3-4, 11.1997, p. 301-308.

Research output: Contribution to journalArticle

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