Inhibition and Stabilization: Cucurbituril Induced Distinct Effects on the Schiff Base Reaction
Wanjun Gong1, Jun Ma1, Zhiyong Zhao1
1The State Key Laboratory of Refractories and Metallurgy, School of Chemistry and Chemical Engineering, Wuhan University of Science and Technology , Wuhan 430081, China.
Abstract:
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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