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Issue 24, 2002
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Receptor versatility of tris(pyridin-1-ium-2-ylmethyl)amine in anion binding through hydrogen bonding

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Abstract

The receptor ability of tris(pyridin-1-ium-2-ylmethyl)amine (triprotonated tris(2-pyridylmethyl)amine, H3TPA3+) toward inorganic anions such as PF6, CF3SO3, Br, and Cl was investigated. Several spectroscopic studies revealed that H3TPA3+ offered characteristic receptor selectivity in the anion complexation. Structural analysis of the receptor-anion complexes [H3TPA(PF6)](PF6)2, [H3TPA(CF3SO3)](CF3SO3)(PF6), [H3TPA(Br)](PF6)2, and [H3TPA(Cl)](PF6)2 indicated that the H3TPA3+ receptor nicely caught each anion guest (X) in its three dimensional cavity via hydrogen bonding (X⋯H⋯N) with pyridinium groups. Treatment of the [H3TPA(X)]2+ (X = PF6 or CF3SO3) complex with a large excess of KBr in the solid state led to the replacement of PF6 or CF3SO3 with Br to give [H3TPA(Br)]2+, whereas Cl in the [H3TPA(Cl)]2+ complex was not replaced. The PF6 anions located in and out of the H3TPA3+ cavity were replaced stepwise with the added Cl or Branion. The strength of the hydrogen bonding increased as the pKb value of the anion decreased in the series Cl > Br > CF3SO3 > PF6.

Graphical abstract: Receptor versatility of tris(pyridin-1-ium-2-ylmethyl)amine in anion binding through hydrogen bonding

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Publication details

The article was received on 23 Sep 2002, accepted on 24 Oct 2002 and first published on 21 Nov 2002


Article type: Paper
DOI: 10.1039/B209331F
Citation: J. Chem. Soc., Dalton Trans., 2002,0, 4535-4540
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    Receptor versatility of tris(pyridin-1-ium-2-ylmethyl)amine in anion binding through hydrogen bonding

    H. Sugimoto, H. Miyake and H. Tsukube, J. Chem. Soc., Dalton Trans., 2002, 0, 4535
    DOI: 10.1039/B209331F

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