Conformational analysis of calix[n] arenes with chiral substituents by using circular dichroism

Atsushi Ikeda, Takeshi Nagasaki, Seiji Shinkai

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39 Citations (Scopus)

Abstract

Calix [n] arenes (n= 4 and 6) bearing chiral substituents (R*) on the lower rim (1n) or on the upper rim (4n) were synthesized. The isomers derived from 14 were conformationally immobile and showed different circular dichroism (CD) spectra. In the 1H NMR spectra the proton signals in R* shifted to higher magnetic field when the lower rim is sterically crowded and in the CD spectra a strong CD band appeared. Therefore, the change in the CD spectra is rationalized in terms of R*…π interactions. In contrast, compound 44 was not conformationally immobilized and the CD spectra changed in response to the metal binding to the methoxy oxygens arranged on the lower rim. The specific metal interaction enabled the metal binding event to be detected by the CD technique.

Original languageEnglish
Pages (from-to)699-710
Number of pages12
JournalJournal of Physical Organic Chemistry
Volume5
Issue number10
DOIs
Publication statusPublished - Oct 1992

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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