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Beyeh NK, Ala-Korpi A, Cetina M, et al. Recognition of N-alkyl and N-aryl acetamides by N-alkyl ammonium resorcinarene chlorides. Chemistry. 2014;20(46):15144-50doi: 10.1002/chem.201402533.
Beyeh, N. K., Ala-Korpi, A., Cetina, M., Valkonen, A., & Rissanen, K. (2014). Recognition of N-alkyl and N-aryl acetamides by N-alkyl ammonium resorcinarene chlorides. Chemistry (Weinheim an der Bergstrasse, Germany), 20(46), 15144-50. https://doi.org/10.1002/chem.201402533
Beyeh, N Kodiah, et al. "Recognition of N-alkyl and N-aryl acetamides by N-alkyl ammonium resorcinarene chlorides." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 20,46 (2014): 15144-50. doi: https://doi.org/10.1002/chem.201402533
Beyeh NK, Ala-Korpi A, Cetina M, Valkonen A, Rissanen K. Recognition of N-alkyl and N-aryl acetamides by N-alkyl ammonium resorcinarene chlorides. Chemistry. 2014 Nov 10;20(46):15144-50. doi: 10.1002/chem.201402533. Epub 2014 Sep 26. PMID: 25257765.
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Chemistry. 2014 Nov 10;20(46):15144-50. doi: 10.1002/chem.201402533. Epub 2014 Sep 26.

Recognition of N-alkyl and N-aryl acetamides by N-alkyl ammonium resorcinarene chlorides.

Chemistry (Weinheim an der Bergstrasse, Germany)

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

Affiliations

  1. Department of Chemistry, Nanoscience Center, University of Jyväskylä, P.O. Box 35, 40014 Jyväskylä (Finland), Fax: (+)?358?14?2602501. [email protected].

PMID: 25257765 DOI: 10.1002/chem.201402533

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.

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: amides; host-guest systems; molecular recognition; resorcinarenes; self-assembly

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