Synthesis and structure of mono-bridged resorcinarene host: a ditopic receptor for ammonium guests

Org Biomol Chem. 2009 Oct 21;7(20):4211-7. doi: 10.1039/b911389d. Epub 2009 Aug 14.

Abstract

The synthesis and structural properties of tetramethoxy resorcinarene mono-crown-5 (1) are described. The binding characteristics of 1 toward acetylcholine and tetramethylammonium salts were investigated by 1H NMR titration. It was observed that the cavity of 1 provides a better fit to acetylcholine compared to the smaller tetramethylammonium cation, as acetylcholine is able to interact with both the crown ether moiety and the free hydroxyl groups of receptor 1 simultaneously.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites
  • Calixarenes / chemical synthesis*
  • Calixarenes / chemistry*
  • Crown Compounds / chemistry
  • Hydroxides / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemical synthesis
  • Phenylalanine / chemistry
  • Quaternary Ammonium Compounds / chemistry*

Substances

  • Crown Compounds
  • Hydroxides
  • Quaternary Ammonium Compounds
  • resorcinarene
  • Calixarenes
  • Phenylalanine
  • hydroxide ion