Helical Conformation of Alkanes in a Hydrophobic Cavitand

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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.

Original languageEnglish
Pages (from-to)1219-1220
Number of pages1
JournalScience
Volume301
DOIs
Publication statusPublished - 2003

Keywords

  • MOLECULAR RECOGNITION
  • ACETYLCHOLINE
  • COMPLEXATION
  • RECEPTORS

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