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

65 Citations (Scopus)

Abstract

We have found that a homotrioxacalix[3]arene (1H 3 ) -based ionophore with a cone conformation, which is very difficult to obtain by the reaction of 1H 3 and ethyl bromoacetate, can be synthesized quantitatively by the reaction of 1H 3 and N,N-diethylchloroacetamide in THF in the presence of NaH. The conformer distribution of the tri-amide derivative (1Am 3 ) between cone and partial-cone was sensitively affected in 0 ∼ 100% range by the metal template effects. Cone-1Am 3 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-1Am 3 acts as an excellent neutral ionophore owing to the three coordinative amide groups arranged in C 3 -symmetry.

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

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Alkaline Earth Metals
Ionophores
Amides
Cations
Cones
Metals
Ions
Derivatives
Alkalies
Esters
Conformations
hexahomotrioxacalix(3)arene

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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. / Matsumoto, Hitoshi; Nishio, Shoko; Takeshita, Michinori; Shinkai, Seiji.

In: Tetrahedron, Vol. 51, No. 16, 17.04.1995, p. 4647-4654.

Research output: Contribution to journalArticle

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N2 - We have found that a homotrioxacalix[3]arene (1H 3 ) -based ionophore with a cone conformation, which is very difficult to obtain by the reaction of 1H 3 and ethyl bromoacetate, can be synthesized quantitatively by the reaction of 1H 3 and N,N-diethylchloroacetamide in THF in the presence of NaH. The conformer distribution of the tri-amide derivative (1Am 3 ) between cone and partial-cone was sensitively affected in 0 ∼ 100% range by the metal template effects. Cone-1Am 3 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-1Am 3 acts as an excellent neutral ionophore owing to the three coordinative amide groups arranged in C 3 -symmetry.

AB - We have found that a homotrioxacalix[3]arene (1H 3 ) -based ionophore with a cone conformation, which is very difficult to obtain by the reaction of 1H 3 and ethyl bromoacetate, can be synthesized quantitatively by the reaction of 1H 3 and N,N-diethylchloroacetamide in THF in the presence of NaH. The conformer distribution of the tri-amide derivative (1Am 3 ) between cone and partial-cone was sensitively affected in 0 ∼ 100% range by the metal template effects. Cone-1Am 3 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-1Am 3 acts as an excellent neutral ionophore owing to the three coordinative amide groups arranged in C 3 -symmetry.

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