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Issue 12, 2005
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Cation–π interaction: a case for macrocyclecation π-interaction by its ureidoarene counteranion

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Abstract

We report the solid state structures of homocomplex [1·K]+[I] and of heterocomplexes [1·K]+[3·I] and [1·K]+[4·I]. In the [1·K]+[I] complex the apical position of the K+ in the macrocycle is occupied by a –CH2– moiety of a neighboring 18-crown-6, consistent with a close contact and corresponding to ‘agostic’ interactions between K+ and –CH2– moieties. In the [1·K]+[3·I] complex the second apical site of the cation is coordinated by a bridging water molecule which is simultaneously H-bonded to both the phenol hydroxyl and the iodide anion. In the [1·K]+[4·I] complex the second apical site of the cation is occupied by the indole moiety. Moreover, the new heterocomplex system [1·K]+[4·I] presented here, despite the multiple possibilities of K+–π contacts with the sterically available phenyl, phenyl-indole and pyrrole-indole rings of 4, shows that the pyrrolo C2[double bond, length as m-dash]C3 double bond is a versatile π-donor. 1H NMR results led us to conclude that the complexes adopt similar conformations in solution to those observed in the solid state.

Graphical abstract: Cation–π interaction: a case for macrocycle–cation π-interaction by its ureidoarene counteranion

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Publication details

The article was received on 30 Jun 2005, accepted on 10 Oct 2005 and first published on 28 Oct 2005


Article type: Paper
DOI: 10.1039/B509240J
Citation: New J. Chem., 2005,29, 1535-1539
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    Cation–π interaction: a case for macrocyclecation π-interaction by its ureidoarene counteranion

    C. Arnal-Herault, M. Barboiu, E. Petit, M. Michau and A. van der Lee, New J. Chem., 2005, 29, 1535
    DOI: 10.1039/B509240J

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