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Kinetically stable complexes in water: The role of hydration and hydrophobicity

Academic Article
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Overview

related to degree

  • Biros, Shannon Marie, Ph.D. in Organic Chemistry, Scripps Research 2001 - 2006
  • Hof, Fraser, Ph.D. in Chemistry, Scripps Research 1998 - 2003

authors

  • Biros, Shannon Marie
  • Ullrich, E. C.
  • Hof, Fraser
  • Trembleau, L.
  • Rebek Jr., Julius

publication date

  • March 2004

journal

  • Journal of the American Chemical Society  Journal

abstract

  • We describe here the synthesis and characterization of a molecular receptor that forms kinetically and thermodynamically stable host-guest complexes in water. This cavitand-based host is composed of a preorganized aromatic pocket whose rim is decorated with four negatively charged carboxylate groups. (1)H NMR and isothermal titration calorimetry have been used to characterize the behavior of the resulting complexes in response to changes in pH, buffer identity, and salt concentration and in the presence of sodium dodecyl sulfate micelles.

subject areas

  • Benzimidazoles
  • Ethers, Cyclic
  • Hydrogen Bonding
  • Hydrogen-Ion Concentration
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Quaternary Ammonium Compounds
  • Resorcinols
  • Thermodynamics
  • Water
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja038823m

PubMed ID

  • 14995204
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Additional Document Info

start page

  • 2870

end page

  • 2876

volume

  • 126

issue

  • 9

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