H-Bonded complexes of adenine with Rebek imide receptors are stabilised by cation-pi interactions and destabilised by stacking with perfluoroaromatics.
A series of Rebek imide receptors with naphthalene or heteroaromatic platforms attached by amide or ester linkers have been prepared from the corresponding acyl chloride or anhydride; the X-ray crystal structure of the receptor-derived anhydride reveals a supramolecular H-bonded helix formation in the crystal; the complexes of adenine bound to the receptors by Hoogsteen H-bonding are found to be stabilised by stacking with a methylquinolinium ion, but destabilised by stacking with a perfluorinated naphthalene.
Faraoni
Raffaella
R
Laboratorium für Organische Chemie, ETH-Hönggerberg, CH-8093 Zürich, Switzerland.
Castellano
Ronald K
RK
Gramlich
Volker
V
Diederich
François
F
D000225:Adenine / Q000737:chemistry*; D002412:Cations / Q000737:chemistry; D018360:Crystallography, X-Ray; D005464:Fluorobenzenes / Q000737:chemistry*; D006860:Hydrogen Bonding; D007094:Imides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure
D002412:Cations; D005464:Fluorobenzenes; D007094:Imides; D000225:Adenine