Isomerization of Glycoluril Dimer and Trimer Related to Cucurbituril Formation

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Authors

GILBERG Laura ŠTANCL Marek GARGULÁKOVÁ Zuzana ŠINDELÁŘ Vladimír

Year of publication 2013
Type Conference abstract
MU Faculty or unit

Faculty of Science

Citation
Description Dimerization of paraformaldehyde and glycoluril in acidic aqueous solution yields an S-shaped dimer as solely kinetic product. In an intermolecular process it transforms to the thermodynamically more stable C-shaped dimer. Same results were observed for trimer. Rate constants for reaction from S- to C-shaped dimer is about one order of magnitude faster than the backward reaction. They accelerate with increasing temperature.Gibbs free energy of isomerization increases with increasing temperature.Activation energy for conversion of C- to S-isomer is 1.5-times higher.Isomerization to C-shaped dimer is enthalpically favoured but entropically disfavoured. During CB-synthesis first two glycoluril units condensate to S-shaped dimer which then converts to the C-shaped. Oligomerization takes place from both isomers at the same time.
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