Tripodal nitro-imidazolium receptor for anion binding driven by (C-H)+- - -X- hydrogen bonds.
[structure: see text] A positively charged tripodal receptor with nitro groups in the imidazolium rings was designed, synthesized, and characterized for its anion binding strength. The receptor shows strong affinity and high selectivity for Cl- through (C-H)+- - -X(-) hydrogen bonds wherein charge-charge and charge-dipole electrostatic interactions dominate. The association constant with chloride anion in a 9:1 mixture of acetonitrile-d3 and DMSO-d6 is measured to be 1.1 x 10(6) M(-1). The receptor also shows reasonably high affinity toward H2PO4-.
National Creative Research Initiative Center for Superfunctional Materials, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, San 31, Hyojadong, Namgu, Pohang 790-784, Korea.
Hyejae
H
Ihm
Sunggoo
S
Yun
Heon Gon
HG
Kim
Jung Kyung
JK
Kim
Kwang S
KS
Kim
D000838:Anions / Q000737:chemistry*; D001665:Binding Sites; D002712:Chlorides / Q000737:chemistry; D006860:Hydrogen Bonding; D009593:Nitroimidazoles / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry; D055672:Static Electricity; D013816:Thermodynamics; D017186:Titrimetry
D000838:Anions; D002712:Chlorides; D009593:Nitroimidazoles; D010710:Phosphates