2-Iodo-imidazolium receptor binds oxoanions via charge-assisted halogen bonding

Org Biomol Chem. 2012 Feb 21;10(7):1329-33. doi: 10.1039/c1ob06524f. Epub 2012 Jan 4.

Abstract

A detailed (1)H-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. 10(3) 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·H(2)PO(4)(-).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions / chemistry
  • Binding Sites
  • Halogens / chemistry*
  • Hydrogen Bonding
  • Imidazoles / chemistry*
  • Iodine Compounds / chemistry*
  • Models, Molecular
  • Phosphates / chemistry

Substances

  • Anions
  • Halogens
  • Imidazoles
  • Iodine Compounds
  • Phosphates
  • imidazole