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Acyl migrations sensitive to supramolecular encapsulation.

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Summary
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Four resorcin[4]arene tetrabenzoates isomers rearrange through base-catalyzed acyl migration. Addition of tetramethylammonium iodide drives equilibrium toward a C2V-symmetric isomer via stable hydrogen-bonded molecular capsules.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Resorcin[4]arene tetrabenzoates exhibit complex isomeric behavior.
  • Acyl migration is a known phenomenon in related molecular systems.

Purpose of the Study:

  • To investigate the interconversion of resorcin[4]arene tetrabenzoate isomers.
  • To understand the role of external factors in shifting isomeric equilibria.

Main Methods:

  • Studied four isomeric resorcin[4]arene tetrabenzoates.
  • Utilized base-catalyzed acyl migration reactions.
  • Employed chloroform solutions and tetramethylammonium iodide extraction.

Main Results:

  • Observed reversible acyl migrations among the isomers.
  • Demonstrated that tetramethylammonium iodide addition shifts equilibrium.
  • Identified the formation of stable hydrogen-bonded molecular capsules as the driving force.

Conclusions:

  • The interconversion of resorcin[4]arene tetrabenzoates is controllable.
  • Hydrogen-bonded molecular capsule formation is key to stabilizing specific isomers.
  • This work provides insights into dynamic equilibria in complex organic molecules.