Recognition of N-Alkyl and N-Aryl Acetamides by N-Alkyl Ammonium Resorcinarene Chlorides

Ngong Kodiah Beyeh, Altti Ala-Korpi, Mario Cetina, Arto Valkonen, Kari Rissanen

Research output: Contribution to journalArticleScientificpeer-review

20 Citations (Scopus)


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[DOUBLE BOND]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.
Original languageEnglish
Pages (from-to)15144–15150
Issue number46
Publication statusPublished - 10 Nov 2014
MoE publication typeA1 Journal article-refereed


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