Calix[3]amide-based anion receptors: High affinity for fluoride ions and a twisted binding model

Kosuke Katagiri, Taniyuki Furuyama, Hyuma Masu, Takako Kato, Mio Matsumura, Masanobu Uchiyama, Aya Tanatani, Masahide Tominaga, Hiroyuki Kagechika, Kentaro Yamaguchi, Isao Azumaya

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Tris-phenylurea-substituted calix[3]amides (3a, 3b) and tris-phenylthiourea-substituted calix[3]amides (4a, 4b) were synthesised by the reaction of amine with isocyanates and thioisocyanate, respectively. Single crystal X-ray analysis revealed that the cyclic trimers adopt a syn conformation with all of the urea groups on the same side. The binding affinities of these compounds towards anions were measured using 1H NMR titrations in DMF-d7, DMSO-d6 or CDCl3. Each receptor was observed to bind halogen anions in a 1:1 stoichiometry, exclusively through hydrogen bonding, and the anion selectivity was in the order F- > Cl- ≫ Br- > I- . DFT calculations revealed that the fluoride anion is anchored in the centre of the six N-H hydrogen atoms of 3a through H...F interactions.

Original languageEnglish
Pages (from-to)125-130
Number of pages6
JournalSupramolecular Chemistry
Volume23
Issue number1-2
DOIs
Publication statusPublished - 2011 Jan

Keywords

  • DFT calculations
  • anion receptor
  • calix[3]amide

ASJC Scopus subject areas

  • Chemistry(all)

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