title: H-Bonded complexes of adenine with Rebek imide receptors are stabilised by cation-pi interactions and destabilised by stacking with perfluoroaromatics.
abstract: 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.
authors.affiliation: Laboratorium für Organische Chemie, ETH-Hönggerberg, CH-8093 Zürich, Switzerland.
authors.forename: Raffaella
authors.initials: R
authors.lastname: Faraoni
authors.forename: Ronald K
authors.initials: RK
authors.lastname: Castellano
authors.forename: Volker
authors.initials: V
authors.lastname: Gramlich
authors.forename: François
authors.initials: F
authors.lastname: Diederich
mesh_terms: 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
chemical_list: D002412:Cations; D005464:Fluorobenzenes; D007094:Imides; D000225:Adenine