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Issue 7, 2012
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2-Iodo-imidazolium receptor binds oxoanionsvia charge-assisted halogen bonding

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Abstract

A detailed 1H-NMR study of the anion binding properties of the 2-iodo-imidazolium receptor 1 in DMSO allows to fully attribute the observed affinities to strong charge-assisted C–I⋯Xhalogen bonding (XB). Stronger binding was observed for oxoanions over halides. Phosphate, in particular, binds to 1 with an association constant of ca. 103 M−1, which is particularly high for a single X-bond. A remarkably short C–I⋯O contact is observed in the structure of the salt 1·H2PO4.

Graphical abstract: 2-Iodo-imidazolium receptor binds oxoanionsvia charge-assisted halogen bonding

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Publication details

The article was received on 05 Sep 2011, accepted on 18 Nov 2011 and first published on 22 Nov 2011


Article type: Paper
DOI: 10.1039/C1OB06524F
Citation: Org. Biomol. Chem., 2012,10, 1329-1333
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    2-Iodo-imidazolium receptor binds oxoanionsvia charge-assisted halogen bonding

    M. Cametti, K. Raatikainen, P. Metrangolo, T. Pilati, G. Terraneo and G. Resnati, Org. Biomol. Chem., 2012, 10, 1329
    DOI: 10.1039/C1OB06524F

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