Recognition of Oxalate by a Copper(II) Polyaza Macrobicyclic Complex
authors Mateus, P; Delgado, R; Brandao, P; Felix, V
nationality International
journal CHEMISTRY-A EUROPEAN JOURNAL
author keywords anionic substrates; cage compounds; cryptands; molecular recognition; sensors
keywords ANION COORDINATION CHEMISTRY; DITOPIC POLYAMMONIUM MACROCYCLES; P-XYLYL SPACERS; MOLECULAR RECOGNITION; DICARBOXYLATE ANIONS; CARBOXYLATE ANIONS; AQUEOUS-SOLUTION; RECEPTOR MOLECULES; SELECTIVE BINDING; CRYSTAL-STRUCTURE
abstract A new polyamine macrobicyclic compound was synthesised through a [1+1] "tripod-tripod coupling" strategy and using a Schiff base condensation reaction, followed by sodium borohydride reduction. The resulting compound is a heteroditopic cage (btpN(7)) in which one of the head units is appropriate for the coordination of copper(II), whereas the other head is available for additional hydrogen-bonding and electrostatic interactions with substrates. The acid-base behaviour of the new compound, the stability constants of its complex with the Cu2+ ion and the association constants of the copper( II) cryptate with oxalate (oxa(2-)), malonate (mal(2-)), succinate (suc(2-)), maleate (male(2-)) and fumarate (fum(2-)) were determined by potentiometry at 298.2 K in aqueous solution and at an ionic strength of 0.10 mol dm(-3) in KNO3. These studies revealed a clear preference of the receptor [CuH(h)btpN(7)H(2)O]((2+h)+) for oxa(2-) over the other dicarboxylate substrates. This arises from co-operativity between metal-anion coordination and electrostatic and hydrogen-bonding interactions, in accordance with the ideal size of this dicarboxylate, which allow it to take full advantage of the potential binding sites of the receptor. A qualitative indicator-displacement study, in agreement with the potentiometric studies, demonstrated that the copper cryptate receptor can be used as a selective visual sensor for oxalate.
publisher WILEY-V C H VERLAG GMBH
issn 0947-6539
year published 2011
volume 17
issue 25
beginning page 7020
ending page 7031
digital object identifier (doi) 10.1002/chem.201100428
web of science category Chemistry, Multidisciplinary
subject category Chemistry
unique article identifier WOS:000292206600020
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journal impact factor 4.857
5 year journal impact factor 4.636
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