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Full Paper
Anion Recognition by Neutral Macrocyclic Azole Amides
Article first published online: 27 NOV 2008
DOI: 10.1002/ejoc.200800811
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Schnopp, M., Ernst, S. and Haberhauer, G. (2009), Anion Recognition by Neutral Macrocyclic Azole Amides. Eur. J. Org. Chem., 2009: 213–222. doi: 10.1002/ejoc.200800811
Publication History
- Issue published online: 2 JAN 2009
- Article first published online: 27 NOV 2008
- Manuscript Received: 22 AUG 2008
Funded by
- Deutsche Forschungsgemeinschaft
- Abstract
- Article
- References
- Cited By
Keywords:
- Anions;
- Host–guest systems;
- Hydrogen bonds;
- Macrocyclic ligands;
- Receptors
Abstract
A straightforward synthesis of C2-symmetric azole-containing macrocyclic peptides is presented. This type of macrocycle possesses four amide groups directed into the interior of the scaffold that act as hydrogen-bond donors and two nitrogen atoms from the azole unit that act as hydrogen-bond acceptors. This arrangement makes them sensitive receptors for Y-shaped anions like AcO– and H2PO4– with a selectivity for dihydrogen phosphate versus acetate, as was shown with 1H NMR titration techniques in [D6]DMSO/5 % CDCl3.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)