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Hydrogen-bonded encapsulation complexes in protic solvents

Academic Article
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Overview

authors

  • Amaya, T.
  • Rebek Jr., Julius

publication date

  • November 2004

journal

  • Journal of the American Chemical Society  Journal

abstract

  • We describe here the behavior of the hydrogen-bonded capsule 1.1 and its complexes in protic solvents. The kinetics and thermodynamics of the encapsulation process were determined through conventional (1)H NMR methods. The enthalpies and entropies of encapsulation are both positive, indicating a process that liberates solvent molecules. The rates of dissociation-association of the capsule were comparable to the rates for the in-out exchange of large guests, which suggests that guest exchange occurs by complete dissociation of the capsule in protic solvents. The stability of the hydrogen-bonded capsule 1.1 toward protic solvents depends strongly on the guests, with the best guest being dimethylstilbene 8. The results establish guidelines for the properties of capsules that could be accessed in water.

subject areas

  • Benzene Derivatives
  • Capsules
  • Deuterium
  • Ethers, Cyclic
  • Hydrogen Bonding
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Methanol
  • Models, Molecular
  • Resorcinols
  • Temperature
  • Thermodynamics
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja0467770

PubMed ID

  • 15506780
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Additional Document Info

start page

  • 14149

end page

  • 14156

volume

  • 126

issue

  • 43

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