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

Research output: Contribution to journalArticleScientificpeer-review

Researchers

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

Research units

  • University of Jyväskylä
  • University of Zagreb
  • Tampere University of Technology

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[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.

Details

Original languageEnglish
Pages (from-to)15144–15150
JournalCHEMISTRY: A EUROPEAN JOURNAL
Volume20
Issue number46
Publication statusPublished - 10 Nov 2014
MoE publication typeA1 Journal article-refereed

ID: 11467736