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Recognition of N ‐Alkyl and N ‐Aryl Acetamides by N ‐Alkyl Ammonium Resorcinarene Chlorides
Author(s) -
Beyeh N. Kodiah,
AlaKorpi Altti,
Cetina Mario,
Valkonen Arto,
Rissanen Kari
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402533
Subject(s) - resorcinarene , chemistry , alkyl , hydrogen bond , aryl , amide , acetamide , ammonium , medicinal chemistry , intermolecular force , crystallography , molecule , organic chemistry
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 (CO) atoms and the amide (NH) groups of the guests, the chloride anions (Cl − ) and ammonium (NH 2 + ) 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.