2-Iodo-imidazolium receptor binds oxoanions via charge-assisted halogen bonding.
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)(-).
NFMLab Department of Chemistry, Materials and Chemical Engineering Giulio Natta, Politecnico di Milano, via Mancinelli 7, I-20131, Milan, Italy.
Massimo
M
Cametti
Kari
K
Raatikainen
Pierangelo
P
Metrangolo
Tullio
T
Pilati
Giancarlo
G
Terraneo
Giuseppe
G
Resnati
D000838:Anions / Q000737:chemistry; D001665:Binding Sites; D006219:Halogens / Q000737:chemistry*; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000737:chemistry*; D017613:Iodine Compounds / Q000737:chemistry*; D008958:Models, Molecular; D010710:Phosphates / Q000737:chemistry
D000838:Anions; D006219:Halogens; D007093:Imidazoles; D017613:Iodine Compounds; D010710:Phosphates; C029899:imidazole