Moving targets: recognition of alkyl groups.
Alkyl chains can adopt seemingly unusual conformations, such as helices, when bound to natural and synthetic hydrophobic receptors. This plasticity allows the alkanes to assume shapes that are congruent to the receptor's space and fill that space properly. We describe here the use of cavitands and capsules as tools that expose the forces involved in the molecular recognition of hydrocarbons. Studies using NMR spectroscopy reveal how attractive interactions and solvophobic forces are maximized in solution through unprecedented contortions of alkanes and hint at a new generation of nanoscale mechanical devices.
Schramm
Michael P
MP
The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Rd. Mail MB 26, La Jolla, CA 92037, USA.
Rebek
Julius
J
D000473:Alkanes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004988:Ethers, Cyclic / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008958:Models, Molecular; D008968:Molecular Conformation; D012015:Reference Standards; D012118:Resorcinols / Q000737:chemistry*; D013237:Stereoisomerism
D000473:Alkanes; D004988:Ethers, Cyclic; D012118:Resorcinols; C442939:cavitand