Cucurbituril-Mediated Supramolecular Acid Catalysis

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 fac...

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Bibliographic Details
Published in:Organic letters 2009-06, Vol.11 (12), p.2595-2598
Main Authors: Klöck, Cornelius, Dsouza, Roy N, Nau, Werner M
Format: Article
Language:English
Subjects:
Bridged-Ring Compounds - chemistry
Cadaverine - chemistry
Cadaverine - pharmacokinetics
Catalysis
Hydrolysis
Imidazoles - chemistry
Macrocyclic Compounds - chemistry
Molecular Structure
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol900920p