title: Recognition of N-alkyl and N-aryl acetamides by N-alkyl ammonium resorcinarene chlorides.
abstract: N-alkyl ammonium resorcinarene chlorides are stabilized by an intricate array of intra- and intermolecular hydrogen bonds that leads to cavitand-like structures. Depending on the upper-rim substituents, self-inclusion was observed in solution and in the solid state. The self-inclusion can be disrupted at higher temperatures, whereas in the presence of small guests the self-included dimers spontaneously reorganize to 1:1 host-guest complexes. These host compounds show an interesting ability to bind a series of N-alkyl acetamide guests through intermolecular hydrogen bonds involving the carbonyl oxygen (C=O) atoms and the amide (NH) groups of the guests, the chloride anions (Cl(-)) and ammonium (NH2(+)) cations of the hosts, and also through CH⋅⋅⋅π interactions between the hosts and guests. The self-included and host-guest complexes were studied by single-crystal X-ray diffraction, NMR titration, and mass spectrometry.
authors.affiliation: Department of Chemistry, Nanoscience Center, University of Jyväskylä, P.O. Box 35, 40014 Jyväskylä (Finland), Fax: (+) 358 14 2602501. ngong.k.beyeh@jyu.fi.
authors.forename: N Kodiah
authors.initials: NK
authors.lastname: Beyeh
authors.forename: Altti
authors.initials: A
authors.lastname: Ala-Korpi
authors.forename: Mario
authors.initials: M
authors.lastname: Cetina
authors.forename: Arto
authors.initials: A
authors.lastname: Valkonen
authors.forename: Kari
authors.initials: K
authors.lastname: Rissanen
keywords: amides; host-guest systems; molecular recognition; resorcinarenes; self-assembly