Journal ArticleDOI
Cucurbit[5]uril, Decamethylcucurbit[5]uril and Cucurbit[6]uril. Synthesis, Solubility and Amine Complex Formation
Klaus Jansen,H.-J. Buschmann,A. Wego,D. Döpp,Christian Mayer,Hans-Joachim Drexler,Hans-Jürgen Holdt,Eckhard Schollmeyer +7 more
TLDR
In this article, a simple way to prepare cucurbit[5]uril is described, and the solubility of cucurbits in aqueous acids has been investigated by means of calorimetric titrations.Abstract:
A simple way to prepare cucurbit[5]uril is described. The macrocycles of the cucurbituril type are nearly insoluble in water. The solubilities of cucurbit[5]uril, decamethylcucurbit[5]uril and cucurbit[6]uril in hydrochloric acid, formic acid and acetic acid of different concentrations have been investigated. Due to the formation of complexes between cucurbit[n]urils and protons the solubility increases in aqueous acids. The macrocyclic ligands are able to form complexes with several organic compounds. Thus, the complex formation of the cucurbituril macrocycles with different amines has beenstudied by means of calorimetric titrations. The reaction enthalpy gives noevidence of the formation of inclusion or exclusion complexes. 1H-NMR measurements show that in the case of cucurbit[5]uril and cucurbit[6]uril the organic guest compound is included within the hydrophobic cavity. Decamethylcucurbit[5]uril forms only exclusion complexes with organicamines. This was confirmed by the crystal structure of the decamethylcucurbit[5]uril-1,6-diaminohexane complex.read more
Citations
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Journal ArticleDOI
The cucurbit[n]uril family
TL;DR: In 1981, the macrocyclic methylene-bridged glycoluril hexamer (CB[6]) was dubbed "cucurbituril" by Mock and co-workers because of its resemblance to the most prominent member of the cucurbitaceae family of plants--the pumpkin.
Journal ArticleDOI
Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry.
TL;DR: This Account is a compilation of recent literature covering the syntheses of the homologues and derivatives, and their supramolecular chemistry of cucurbituril, a synthetic receptor.
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Cucurbituril-Based Molecular Recognition.
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Cucurbituril chemistry: a tale of supramolecular success
TL;DR: Cucurbit[n]urils have become key units in various self-organizing and stimulus-controlled assemblies, as well as in advanced materials and drug carriers.
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Mechanism of host-guest complexation by cucurbituril.
TL;DR: The factors affecting host-guest complexation between the molecular container compound cucurbit[6]uril (CB6) and various guests in aqueous solution are studied, and a detailed complexation mechanism in the presence of cations is derived.
References
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Journal ArticleDOI
New Cucurbituril Homologues: Syntheses, Isolation, Characterization, and X-ray Crystal Structures of Cucurbit[n]uril (n = 5, 7, and 8)
Jaheon Kim,In-Sun Jung,Soo Young Kim,Eunsung Lee,Jin-Koo Kang,Shigeru Sakamoto,and Kentaro Yamaguchi,Kimoon Kim +7 more
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Structure and selectivity in host―guest complexes of cucurbituril
William L. Mock,Neng Yang Shih +1 more
TL;DR: Etude du mode de liaison d'ions alkylammonium a l'interieur de la cavite du cucurbiturile obtenu par condensations entre l'uree, le glyoxal and le formaldehyde as discussed by the authors.
Journal ArticleDOI
Host-guest binding capacity of cucurbituril
W. L. Mock,N. Y. Shih +1 more
TL;DR: Constantes de dissociation du cucurbiturile avec divers alkylammoniums and polymethylene bis-ammonium as discussed by the authors, i.e.
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Organic ligand-receptor interactions between cucurbituril and alkylammonium ions
William L. Mock,Neng Yang Shih +1 more
Journal ArticleDOI
Cucurbituril as a ligand for the complexation of cations in aqueous solutions
TL;DR: The complex formation of the ligand cucurbituril with alkaline cations and other cations have been studied by means of solubility measurements in the presence of the salts in aqueous solutions at 25 °C.