Selective recognition of carboxylate anions by polyammonium receptors in aqueous solution. Criteria for selectivity in molecular recognition
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 3,p. 569-577
- https://doi.org/10.1039/p29940000569
Abstract
The interaction in aqueous solution of the polyammonium receptor 1,4,7,10,13,16,19-heptaazacyclohenicosane (8, [21]aneN7) with the carboxylic species, 1,2-benzenedicarboxylic (1), 1,3-benzenedicarboxylic (2), 1,2,3-benzenetricarboxylic (3), 1,3,5-benzenetricarboxylic (4), cis,cis-1,3,5-trimethyl-1,3,5-cyclohexanetricarboxylic (5), cis,trans-1,3,5-trimethyl-1,3,5-cyclohexanetricarboxylic (6), and citric (7) acids has been followed by potentiometry and cyclic voltammetry at 298.1 K in 0.15 mol dm–3 NaClO4, as well as by NMR spectroscopy. The analysis of the potentiometric and electrochemical data show the formation of 1:1 adducts. A novel method based on both potentiometry and cyclic voltammetry to establish selectivity patterns in systems presenting different protonation possibilities is introduced. Preorganization of the substrates in a shape complementary to the receptor yields interesting features such as the selective recognition of 5 over its epimer 6 and recognition of the dicarboxylic species 1 and 2 over the tricarboxylic ones 6 and 7.Keywords
This publication has 59 references indexed in Scilit:
- Molecular catalysis by polyammonium receptorsPublished by Springer Nature ,2005
- A remarkable shape selectivity in the molecular recognition of carboxylate anions in aqueous solutionJournal of the American Chemical Society, 1992
- Molecular recognition of anionic substrates. Binding of carboxylates by a macrobicyclic coreceptor and crystal structure of its supramolecular cryptate with the terephthalate dianionJournal of the Chemical Society, Chemical Communications, 1991
- Molecular recognition in aqueous solution: Supramolecular complexation and catalysisPublished by American Chemical Society (ACS) ,1990
- Anion‐receptor molecules: Macrocyclic and macrobicyclic effects on anion binding by polyammonium receptor moleculesHelvetica Chimica Acta, 1988
- Anion Coreceptor Molecules. Linear Molecular Recognition in the Selective Binding of Dicarboxylate Substrates by Ditopic Polyammonium MacrocyclesHelvetica Chimica Acta, 1986
- Anion receptor molecules. Chain length dependent selective binding of organic and biological dicarboxylate anions by ditopic polyammonium macrocyclesJournal of the American Chemical Society, 1982
- Macromonocyclic polyamines as specific receptors for tricarboxylate-cycle anionsJournal of the American Chemical Society, 1981
- Selective functionalization of doubly coordinated flexible chainsJournal of the American Chemical Society, 1981
- Anion receptor molecules. Synthesis and anion-binding properties of polyammonium macrocyclesJournal of the American Chemical Society, 1981