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Anion Recognition by Neutral Macrocyclic Azole Amides
Author(s) -
Schnopp Markus,
Ernst Silvia,
Haberhauer Gebhard
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800811
Subject(s) - chemistry , azole , hydrogen bond , amide , titration , selectivity , proton nmr , ion , stereochemistry , combinatorial chemistry , medicinal chemistry , molecule , organic chemistry , catalysis , antifungal , medicine , dermatology
Abstract A straightforward synthesis of C 2 ‐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 H 2 PO 4 – with a selectivity for dihydrogen phosphate versus acetate, as was shown with 1 H NMR titration techniques in [D 6 ]DMSO/5 % CDCl 3 .(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)