Formation and trapping of the thermodynamically unfavoured inverted-hemicucurbit[6]uril

Elena Prigorchenko; Sandra Kaabel; Triin Narva; Anastassia Baškir; Maria Fomitšenko; Jasper Adamson; Ivar Järving; Kari Rissanen; Toomas Tamm; Riina Aav

doi:10.1039/C9CC04990H

Formation and trapping of the thermodynamically unfavoured inverted-hemicucurbit[6]uril†

Elena Prigorchenko,

‡^a Sandra Kaabel,

^a Triin Narva,^a Anastassia Baškir,^a Maria Fomitšenko,

^a Jasper Adamson,

^b Ivar Järving,^a Kari Rissanen,

^c Toomas Tamm

^a and Riina Aav

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
E-mail: riina.aav@taltech.ee

^b National Institute of Chemical Physics and Biophysics, Akadeemia tee 23, 12618 Tallinn, Estonia

^c Department of Chemistry, University of Jyvaskyla, P.O. Box 35, 40014 Jyvaskyla, Finland

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.

Chemical Communications

Formation and trapping of the thermodynamically unfavoured inverted-hemicucurbit[6]uril†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Formation and trapping of the thermodynamically unfavoured inverted-hemicucurbit[6]uril

Social activity

Search articles by author

Spotlight

Advertisements