Syntheses and ion selectivities of tri-amide derivatives of hexahomotrioxacalix[3]arene. Remarkably large metal template effect on the ratio of cone vs. Partial-cone conformers

Hitoshi Matsumoto, Shoko Nishio, Michinori Takeshita, Seiji Shinkai

Research output: Contribution to journalArticle

67 Citations (Scopus)

Abstract

We have found that a homotrioxacalix[3]arene (1H3) -based ionophore with a cone conformation, which is very difficult to obtain by the reaction of 1H3 and ethyl bromoacetate, can be synthesized quantitatively by the reaction of 1H3 and N,N-diethylchloroacetamide in THF in the presence of NaH. The conformer distribution of the tri-amide derivative (1Am3) between cone and partial-cone was sensitively affected in 0 ∼ 100% range by the metal template effects. Cone-1Am3 showed the very high affinity for alkali and alkaline earth metal cations. Particularly, it formed stable complexes with alkaline earth metal cations which were scarcely bound to the tri-ester derivative. The results show that cone-1Am3 acts as an excellent neutral ionophore owing to the three coordinative amide groups arranged in C3-symmetry.

Original languageEnglish
Pages (from-to)4647-4654
Number of pages8
JournalTetrahedron
Volume51
Issue number16
DOIs
Publication statusPublished - Apr 17 1995
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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