Issue 23, 2011

meta-Substituted benzamide oligomers that complex mono-, di- and tricarboxylates: folding-induced selectivity and chirality

Abstract

meta-Substituted arylamide trimer, pentamer and heptamer have been prepared from simple benzene-1,3-diamine, benzene-1,3-dicarboxylic acid, and 3-aminobenzoic acid units. 2D NOESY 1H NMR experiments reveal that these flexible oligomers form folded conformations to complex di- and tricarboxylate anions of varying sizes and shapes in DMSO of high polarity, which is driven by multiple intermolecular N–H⋯O[double bond, length as m-dash]C and C–H⋯O[double bond, length as m-dash]C hydrogen-bonds between the amide and aromatic hydrogens of the oligomers and the carboxylate oxygens of the anions. Generally, tricarboxylate anions display an increased binding affinity compared with the dicarboxylate anions and the complexes formed by 1,3-benzenedicarboxylate anion are more stable than those formed by 1,2- or 1,4-benzenedicarboxylate anions. Circular dichroism experiments show that chiral glutamic acid dianion can induce the oligomers to produce chiral bias, leading to the formation of chiral supramolecular complexes.

Graphical abstract: meta-Substituted benzamide oligomers that complex mono-, di- and tricarboxylates: folding-induced selectivity and chirality

Supplementary files

Article information

Article type
Paper
Submitted
26 Jun 2011
Accepted
06 Sep 2011
First published
06 Sep 2011

Org. Biomol. Chem., 2011,9, 8122-8129

meta-Substituted benzamide oligomers that complex mono-, di- and tricarboxylates: folding-induced selectivity and chirality

Z. Shi, S. Chen, X. Zhao, X. Jiang and Z. Li, Org. Biomol. Chem., 2011, 9, 8122 DOI: 10.1039/C1OB06026K

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