Inhibition of C(2)-H/D exchange of a bis(imidazolium) dication upon complexation with cucubit[7]uril

Literature Information

Publication Date 2006-06-02
DOI 10.1039/B605919H
Impact Factor 6.222
Authors

Ruibing Wang, Lina Yuan, Donal H. Macartney


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Abstract

Inclusion of the α,α′-bis(3-(1-methylimidazolium))-p-xylene dication in cucurbit[7]uril (CB[7], KCB[7] = (4.3 × 109 M−1), with C–H⋯OC hydrogen bonding between the guest C(2)-protons and the carbonyl oxygens of the host portals, inhibits the H/D exchange for the C(2)-proton with kOD (25 °C, D2O) decreasing from 1.2 × 103 M−1 s−1 (pKa = 22.3) in the absence of CB[7] to 0.9 M−1 s−1 (pKa = 25.4) in the presence of 1.1 equiv. CB[7].

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Contents and Highlights in Chemical Biology

Front/Back Matter

DOI: 10.1039/B918025G

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