Propanediurea-Based Molecular Clips Bind Halide Anions: An Insight into the Mechanism of Cucurbituril Formation

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Authors

LÍZAL Tomáš USTRNUL Lukáš NEČAS Marek ŠINDELÁŘ Vladimír

Year of publication 2016
Type Article in Periodical
Magazine / Source Journal of Organic Chemistry
MU Faculty or unit

Faculty of Science

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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