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 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.
Klöck
Cornelius
C
School of Engineering and Science, Jacobs University Bremen, Campus Ring 1, D-28759 Bremen, Germany.
Dsouza
Roy N
RN
Nau
Werner M
WM
D001952:Bridged-Ring Compounds / Q000737:chemistry; D002103:Cadaverine / Q000737:chemistry / Q000493:pharmacokinetics*; D002384:Catalysis; D006868:Hydrolysis; D007093:Imidazoles / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D000099246:Cucurbit(n)urils
D001952:Bridged-Ring Compounds; D002103:Cadaverine; D007093:Imidazoles; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils; C456276:cucurbit(7)uril; C454805:cucurbit(6)uril