Polyfunctional recognition of pyridinedicarboxylate anions with macrocyclic polyamine receptors containing heteroaromatic groups

Bazzicalupi, Carla and Bencini, Andrea and Bianchi, Antonio and Borri, Claudia and Danesi, Andrea and Garcia-España, Enrique and Giorgi, Claudia and Valtancoli, Barbara Polyfunctional recognition of pyridinedicarboxylate anions with macrocyclic polyamine receptors containing heteroaromatic groups. Journal of Organic Chemistry, 73 (21). pp. 8286-8295. ISSN 0022-3263 (2008)

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Abstract

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 21aneN7 (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 H83(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.

Item Type:	Article
Identification Number:	10.1021/jo801366w
Additional Information:	PMID: 18841919
Subjects:	Q Science > QD Chemistry
Research Area:	Computer Science and Applications
Depositing User:	Ms T. Iannizzi
Date Deposited:	03 Mar 2014 13:54
Last Modified:	03 Mar 2014 13:54
URI:	http://eprints.imtlucca.it/id/eprint/2167

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