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- Title
Synthesis of Cucurbit[6]uril Derivatives and Insights into Their Solubility in Water.
- Authors
Lewin, Véronique; Rivollier, Julie; Coudert, Sylvie; Buisson, David‐Alexandre; Baumann, Delphine; Rousseau, Bernard; Legrand, François‐Xavier; Kouřilová, Hana; Berthault, Patrick; Dognon, Jean‐Pierre; Heck, Marie‐Pierre; Huber, Gaspard
- Abstract
Four new cucurbiturils Cy nCB[6] containing n ( n = 1, 2, 4, 5) cyclohexyl equatorial units have been synthesized to complete the family of known Cy3CB[6] and Cy6CB[6] derivatives. A new CB[6] member bearing a propanediurea unit has also been prepared. The CB[6] derivatives show better solubility in pure water than native CB[6]. One cyclohexyl unit is sufficient to enhance the solubility in water by a factor of 170 with respect to CB[6], and Cy6CB[6] is around 30 times more soluble than Cy1CB[6]. The cyclohexane moieties, by limiting or impeding the formation of intermolecular C-H ···O hydrogen bonds, may explain this increase in solubility. The effect of modification of the molecular shape on the solubility was assessed by liquid-state NMR spectroscopy and DFT calculations.
- Subjects
CUCURBITACEAE; SOLUBILITY; NUCLEAR magnetic resonance spectroscopy; CYCLOHEXYLAMINE; HYDROGEN bonding
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 18, p3857
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201300229