Polyfunctional Recognition of Pyridinedicarboxylate Anions with Macrocyclic Polyamine Receptors Containing Heteroaromatic Groups

The interaction of the biologically relevant anions deriving from the six pyridinedicarboxylic acids (H2PDC) with two macrocyclic receptors containing a pentamine chain and a bipyridine (1) or a phenanthroline (2) moiety, as well as with the aliphatic analogue [21]aneN7 (3), was studied by means of...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-11, Vol.73 (21), p.8286-8295
Main Authors: Bazzicalupi, Carla, Bencini, Andrea, Bianchi, Antonio, Borri, Claudia, Danesi, Andrea, Garcia-España, Enrique, Giorgi, Claudia, Valtancoli, Barbara
Format: Article
Language:English
Subjects:
Aliphatic compounds
Anions
Binding Sites
Carboxylic Acids - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hydrocarbons, Aromatic - chemistry
Hydrogen Bonding
Macrocyclic Compounds - chemistry
Models, Molecular
Organic chemistry
Polyamines - chemistry
Potentiometry
Preparations and properties
Pyridines - chemistry
Spectrum Analysis
Static Electricity
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Summary:The interaction of the biologically relevant anions deriving from the six pyridinedicarboxylic acids (H2PDC) with two macrocyclic receptors containing a pentamine chain and a bipyridine (1) or a phenanthroline (2) moiety, as well as with the aliphatic analogue [21]aneN7 (3), was studied by means of spectroscopic methods (UV−vis, NMR) and potentiometric titrations affording the stability constants of the adducts formed. All three receptors form stable complexes with the substrates thanks to the formation of several salt bridges and hydrogen bond contacts, as observed in the crystal structure of the H8[3(2,6-PDC)4]·H2O·0.5EtOH solid compound. Additional π-stacking interactions between the aromatic moieties of substrates and receptors enhance the stability of complexes with 1 and 2. Compounds 1 and 2 show a marked selectivity toward 2,6- pyridinedicarboxylate anions. In particular, 1 is able to perform a very efficient recognition of these species in the presence of 2 and 3. Molecular modeling calculations suggested that such recognition ability of 1 can be ascribed to a superior structural and electrostatic complementarity with the substrate compared to 2 and 3.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo801366w