Issue 7, 2012
From the journal:

Organic & Biomolecular Chemistry

2-Iodo-imidazolium receptor binds oxoanionsvia charge-assisted halogen bonding†

Massimo Cametti,a   Kari Raatikainen,a   Pierangelo Metrangolo,*ab   Tullio Pilati,a   Giancarlo Terraneoab  and  Giuseppe Resnati*ab  

* Corresponding authors

a NFMLab Department of Chemistry, Materials and Chemical Engineering “Giulio Natta”, Politecnico di Milano, via Mancinelli 7, Milan, Italy
E-mail: pierangelo.metrangolo@polimi.it, giuseppe.resnati@polimi.it

b Center for Nano Science and Technology@Polimi, Istituto Italiano di Tecnologia, via Pascoli 70/3, Milano, Italy

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⋯X−halogen 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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Article information

DOI
https://doi.org/10.1039/C1OB06524F
Article type
Paper
Submitted
05 Sep 2011
Accepted
18 Nov 2011
First published
22 Nov 2011

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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