Helical Conformation of Alkanes in a Hydrophobic Cavitand

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 surfacta...

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Bibliographic Details
Published in:Science (American Association for the Advancement of Science) 2003-08, Vol.301 (5637), p.1219-1220
Main Authors: Trembleau, Laurent, Rebek, Julius
Format: Article
Language:English
Subjects:
Alkanes
Alkanes - chemistry
Benzimidazoles - chemistry
Biochemistry
Carbon
Chemical Phenomena
Chemical properties
Chemicals
Chemistry
Chemistry, Physical
Conformational analysis
Exact sciences and technology
General and physical chemistry
Hydrogen Bonding
Hydrophobic and Hydrophilic Interactions
Inhalants
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Conformation
Molecules
Nuclear magnetic resonance
Observational research
Phosphorylcholine - analogs & derivatives
Phosphorylcholine - chemistry
Receptors
Scientific Concepts
Sodium Dodecyl Sulfate - chemistry
Solutions
Surface physical chemistry
Surface Properties
Surface-Active Agents - chemistry
Surface-active agents: properties
Temperature
Thermodynamics
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Summary: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.
ISSN:0036-8075
1095-9203
DOI:10.1126/science.1086644