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Formation and trapping of the thermodynamically unfavoured inverted-hemicucurbit[6]uril
Elena Prigorchenko1, Sandra Kaabel1, Triin Narva1
1Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia. riina.aav@taltech.ee.
Abstract:
Formation of inverted-cis-cyclohexanohemicucurbit[6]uril (i-cis-cycHC[6]), with up to 33% isolated yield, can be induced at the expense of thermodynamically favoured cis-cycHC[6]. Reaction selectivity is governed by the solution-based template-aided dynamic combinatorial chemistry and continuous precipitation of the formed macrocycles. Different binding affinities of three diastereomeric cycHC[6]s with trifluoroacetic acid is demonstrated.
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