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Issue 8, 2017
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Cu2+ recognition by N,N′-benzylated bis(amino amides)

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Abstract

Two new C2-symmetric N,N′-benzylated bis(amino amides) have been synthesised and their interaction with different transition metals studied using a variety of techniques including UV-Vis and CD spectroscopy or ESI-MS. The determination of the corresponding stability constants with Cu2+ has been possible, in H2O/CH3CN 7/3 v/v, for one of these ligands (4) using potentiometric titrations. The results obtained reveal that N-benzylation affords significant changes to their properties and is accompanied by an appreciable decrease in the corresponding complexation stability constants. However, this, along with the low kinetics associated to Ni2+, facilitates the recognition of Cu2+ by 4 that can be followed by the naked-eye up to the submillimolar range. Very interestingly, the chiral nature of this ligand provides an intense and well defined CD curve for the corresponding Cu2+ complex, very sensitive to the coordination geometry, facilitating the analysis of this interaction even at the μM range. The formation by both ligands (3 and 4) of square planar complexes with Cu2+ and Ni2+ displaying a 1 : 1 stoichiometry was confirmed by their X-ray crystal structures.

Graphical abstract: Cu2+ recognition by N,N′-benzylated bis(amino amides)

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Publication details

The article was received on 16 Dec 2016, accepted on 31 Jan 2017 and first published on 31 Jan 2017


Article type: Paper
DOI: 10.1039/C6DT04756D
Citation: Dalton Trans., 2017,46, 2660-2669
  • Open access: Creative Commons BY license
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    Cu2+ recognition by N,N′-benzylated bis(amino amides)

    L. Gorla, V. Martí-Centelles, B. Altava, M. I. Burguete and S. V. Luis, Dalton Trans., 2017, 46, 2660
    DOI: 10.1039/C6DT04756D

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