Synthesis and structure of mono-bridged resorcinarene host: a ditopic receptor for ammonium guests.
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.
Department of Chemistry, Nanoscience Center, University of Jyväskylä, P.O. Box 35, 40014 JYU, Finland.
Kirsi
K
Salorinne
Tiia-Riikka
TR
Tero
Kaisa
K
Riikonen
Maija
M
Nissinen
D001665:Binding Sites; D047250:Calixarenes / Q000138:chemical synthesis* / Q000737:chemistry*; D047248:Crown Compounds / Q000737:chemistry; D006878:Hydroxides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
D047248:Crown Compounds; D006878:Hydroxides; D000644:Quaternary Ammonium Compounds; C466160:resorcinarene; D047250:Calixarenes; D010649:Phenylalanine; C031356:hydroxide ion