Cucurbituril-mediated supramolecular acid catalysis

Org Lett. 2009 Jun 18;11(12):2595-8. doi: 10.1021/ol900920p.

Abstract

The rates of acid hydrolysis of N-benzoyl-cadaverine (1), mono-N-(tert-butoxy)carbonyl cadaverine (2), and benzaldoxime (3) with binding motifs for cucurbit[6]uril (1,2) and cucurbit[7]uril (1,3) were investigated in the absence and presence of these hosts. Significant rate enhancements (up to a factor of ca. 300 for the hydrolysis of 3) were observed. Competitive inhibition due to encapsulation of added cadaverine and the successful use of sub-stoichiometric amounts of macrocycle confirmed the function of cucurbiturils in promoting acid hydrolysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged-Ring Compounds / chemistry
  • Cadaverine / chemistry
  • Cadaverine / pharmacokinetics*
  • Catalysis
  • Hydrolysis
  • Imidazoles / chemistry
  • Macrocyclic Compounds / chemistry*
  • Molecular Structure

Substances

  • Bridged-Ring Compounds
  • Imidazoles
  • Macrocyclic Compounds
  • cucurbit(7)uril
  • cucurbit(n)uril
  • cucurbit(6)uril
  • Cadaverine