Kinetically stable complexes in water: the role of hydration and hydrophobicity.
We describe here the synthesis and characterization of a molecular receptor that forms kinetically and thermodynamically stable host-guest complexes in water. This cavitand-based host is composed of a preorganized aromatic pocket whose rim is decorated with four negatively charged carboxylate groups. (1)H NMR and isothermal titration calorimetry have been used to characterize the behavior of the resulting complexes in response to changes in pH, buffer identity, and salt concentration and in the presence of sodium dodecyl sulfate micelles.
The Skaggs Institute for Chemical Biology and the Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Shannon M
SM
Biros
Elke C
EC
Ullrich
Fraser
F
Hof
Laurent
L
Trembleau
Julius
J
Rebek
D001562:Benzimidazoles / Q000737:chemistry; D004988:Ethers, Cyclic / Q000737:chemistry*; D006860:Hydrogen Bonding; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D012118:Resorcinols / Q000737:chemistry*; D013816:Thermodynamics; D014867:Water / Q000737:chemistry*
D001562:Benzimidazoles; D004988:Ethers, Cyclic; D000644:Quaternary Ammonium Compounds; D012118:Resorcinols; C442939:cavitand; D014867:Water