Interaction energies and dynamics of acid-base pairs isolated in cavitands

J Org Chem. 2008 Sep 5;73(17):6480-8. doi: 10.1021/jo8008534. Epub 2008 Aug 2.

Abstract

The use of capsules and cavitands in physical organic chemistry is briefly reviewed, and their application to the study of salt bridges is introduced. Carboxylate/ammonium ion pairs are generated within an environment that more or less surrounds the functional groups within a synthetic fixed introverted solvent sphere. This is provided by cavitands that fold around amines and present them with a carboxylic acid function. Both organic and water-soluble versions were prepared, and their equilibrium affinities with quinuclidine bases were determined by NMR methods. The association constants range from approximately 10(3) M(-1) in water to more than 10(5) M(-1) in organic solvents. Studies of nitrogen inversion and tumbling of [2.2.2]-diazabicyclooctane within the introverted acids also illustrate the strength of the acid-base interactions. The barriers to in-out exchange of several amine guests were determined to be in the range from 15 to 24 kcal mol(-1). Some parallels with enzymes are drawn: the receptor folds around the guest species; presents them with inwardly directed functionality; and provides a generally hydrophobic environment and a periphery of secondary amide bonds.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Amines / chemistry*
  • Carboxylic Acids / chemistry*
  • Ethers, Cyclic / chemistry*
  • Hydrogen Bonding
  • Hydrophobic and Hydrophilic Interactions
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Resorcinols / chemistry*
  • Solvents / chemistry
  • Thermodynamics

Substances

  • Amides
  • Amines
  • Carboxylic Acids
  • Ethers, Cyclic
  • Resorcinols
  • Solvents
  • cavitand