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Synthesis of Cucurbit[6]uril Derivatives and Insights into Their Solubility in Water
Author(s) -
Lewin Véronique,
Rivollier Julie,
Coudert Sylvie,
Buisson DavidAlexandre,
Baumann Delphine,
Rousseau Bernard,
Legrand FrançoisXavier,
Kouřilová Hana,
Berthault Patrick,
Dog JeanPierre,
Heck MariePierre,
Huber Gaspard
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300229
Subject(s) - solubility , chemistry , cyclohexane , cucurbituril , intermolecular force , hydrogen bond , supramolecular chemistry , medicinal chemistry , stereochemistry , organic chemistry , molecule
Four new cucurbiturils Cy n CB[6] containing n ( n = 1, 2, 4, 5) cyclohexyl equatorial units have been synthesized to complete the family of known Cy 3 CB[6] and Cy 6 CB[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 Cy 6 CB[6] is around 30 times more soluble than Cy 1 CB[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.