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Inhibition and Stabilization: Cucurbituril Induced Distinct Effects on the Schiff Base Reaction

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journal contribution
posted on 23.02.2017 by Wanjun Gong, Jun Ma, Zhiyong Zhao, Fang Gao, Feng Liang, Haijun Zhang, Simin Liu
The different effects of cucurbit[7]­uril (CB[7]) on the Schiff base reactions in aqueous solution were explored by 1H NMR spectroscopy and single X-ray crystallography. With CB[7], the condensation reaction of aldehyde and primary amine is dramatically inhibited. In contrast, the presence of CB[7] does tremendously stabilize iminium cation in water through ion–dipole interactions. A single crystal structure of the complex of iminium ion 7 with CB[7] grown in water is reported.

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