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Helical conformation of alkanes in a hydrophobic cavitand

Academic Article
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Overview

authors

  • Trembleau, L.
  • Rebek Jr., Julius

publication date

  • August 2003

journal

  • Science  Journal

abstract

  • Alkanes adopt extended conformations in solution that minimize steric interactions and maximize surface area. Folding can reduce the amount of hydrophobic surface exposed to solvent, but sterically unfavorable gauche interactions result. However, we found that the alkyl chains of two common surfactants in aqueous solution adopt helical conformations when bound within a synthetic receptor. The receptor recognizes the helical alkane better than the extended conformation, even though 2 to 3 kilocalories per mole of strain is introduced. The proper filling of space and burial of hydrophobic surface drive the molecular recognition between the receptor and the coiled alkane.

subject areas

  • Alkanes
  • Benzimidazoles
  • Chemistry, Physical
  • Hydrogen Bonding
  • Hydrophobic and Hydrophilic Interactions
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Phosphorylcholine
  • Physicochemical Phenomena
  • Sodium Dodecyl Sulfate
  • Solutions
  • Surface Properties
  • Surface-Active Agents
  • Temperature
  • Thermodynamics
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Identity

International Standard Serial Number (ISSN)

  • 0036-8075

Digital Object Identifier (DOI)

  • 10.1126/science.1086644

PubMed ID

  • 12947192
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Additional Document Info

start page

  • 1219

end page

  • 1220

volume

  • 301

issue

  • 5637

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