"Cone" - "Partial-cone" Isomerism in Tetramethoxycalix[4]arenes. Influence of Solvent Polarity and Metal Ions

Koji Iwamoto, Atsushi Ikeda, Koji Araki, Takaaki Harada, Seiji Shinkai

Research output: Contribution to journalArticlepeer-review

58 Citations (Scopus)

Abstract

It was found that the "cone" - "partial-cone" equilibrium in 25,26,27,28-tetramethoxycalix[4]arene derivatives is sensitively affected by the solvent polarity: the cone% increases with the increase in the solvent polarity. The novel finding was rationalized in terms of the difference in the dipole moment: cone conformers with four dipole moments orientating into the same direction are more polar than partial-cone conformers with one inverted phenyl unit and therefore are more stabilized in polar solvents. Alkali metal cations such as Li+ and Na+ strongly interact with four methoxy oxygens, resulting in the shift of the equilibrium to cone.

Original languageEnglish
Pages (from-to)9937-9946
Number of pages10
JournalTetrahedron
Volume49
Issue number44
DOIs
Publication statusPublished - 1993

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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