Propanediurea-Based Molecular Clips Bind Halide Anions: An Insight into the Mechanism of Cucurbituril Formation
| Authors | |
|---|---|
| Year of publication | 2016 |
| Type | Article in Periodical |
| Magazine / Source | Journal of Organic Chemistry |
| MU Faculty or unit | |
| Citation | |
| Web | http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b01602 |
| Doi | http://dx.doi.org/10.1021/acs.joc.6b01602 |
| Field | Organic chemistry |
| Keywords | BRIDGED GLYCOLURIL DIMERS; DIASTEREOSELECTIVE FORMATION; HIGH-AFFINITY; HOST; DERIVATIVES; WATER; ISOMERIZATION; RECOGNITION; SOLUBILITY; MACROCYCLE |
| Description | The synthesis and supramolecular properties of the first methylene-bridged propanediurea-based dimers are described. These dimers, bearing an aromatic sidewall, have the shape of molecular clips. Unlike glycoluril-based dimers, these clips neither dimerize nor accept any organic guests, due to their small cavities. Both propanediurea- and glycoluril-based dimers bind halide anions on the convex side of the molecules, even in highly polar organic solvents. This observation brings new insights into the mechanism of cucurbituril formation. |
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