title: Folded alkyl chains in water-soluble capsules and cavitands.
abstract: A deep cavitand with ionic "feet" dimerizes around hydrophobic compounds in D2O. Longer n-alkane guests, C14-C18, are encapsulated in contorted conformations and NMR is used to deduce their shapes. Competition experiments establish the driving forces involved and how they compensate for the steric clashes in the folded structures of the encapsulated alkanes. Bolaamphiphiles instead prefer to bind in the monomeric cavitand with conformations that bury the methylenes but expose the polar head groups to solvent.
authors: Skaggs Institute for Chemical Biology, and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA. jrebek@scripps.edu.
authors: Jesse V
authors: JV
authors: Gavette
authors: Kang-Da
authors: KD
authors: Zhang
authors: Dariush
authors: D
authors: Ajami
authors: Julius
authors: J
authors: Rebek
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D019281:Dimerization; D004988:Ethers, Cyclic / Q000737:chemistry*; D006860:Hydrogen Bonding; D057927:Hydrophobic and Hydrophilic Interactions; D008958:Models, Molecular; D008968:Molecular Conformation; D012118:Resorcinols / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D000473:Alkanes; D004988:Ethers, Cyclic; D012118:Resorcinols; D014867:Water