Journal ArticleDOI
Controlling factors in the synthesis of cucurbituril and its homologues.
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TLDR
A wide range of reaction conditions are examined that include the effects of acid type, acid concentration, reactant concentrations, and temperature to both probe the mechanism and optimize the yields of isolated cucurbit[n]urils, where n = 5-10.Abstract:
The acid-catalyzed synthesis of cucurbit[n]urils from formaldehyde and glycoluril is poorly understood. In this paper, we examine a wide range of reaction conditions that include the effects of acid type, acid concentration, reactant concentrations, and temperature to both probe the mechanism and optimize the yields of isolated cucurbit[n]urils, where n = 5−10. A mechanism for the formation of these cucurbit[n]urils is presented. Individual cucurbit[n]urils were unambiguously identified in reaction mixtures using ESMS and 13C NMR.read more
Citations
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Inclusion complexes of cationic xanthene dyes in cucurbit[7]uril
Ronald L. Halterman,Jason L. Moore,Krystle A. Yakshe,Julie A. I. Halterman,Kevin Andrew Woodson +4 more
TL;DR: In this paper, uniformly applied ensemble spectroscopic studies are presented, including 1H NMR, UV-Vis, and fluorescence titration experiments of aqueous cucurbit[7]uril complexes with the monocationic xanthene dyes rhodamine 6G (Rh6G), rhB, rhBBE and pyronin Y (PyY).
Journal ArticleDOI
Formation thermodynamics of cucurbit[6]uril macrocycle molecules: a theory study.
TL;DR: A thermodynamical analysis of macromolecule cyclization from a monomer to a pentamer and CB6 found that water molecules, which are formed as one of the products of the reaction of glicoluril with formaldehyde, construct dimer and oligomer CB(m) so that an angle between adjacent building units corresponds to the stable homologue CB[6].
Journal ArticleDOI
Encapsulation of a β-carboline in cucurbit[7]uril
TL;DR: Inclusion of a biological photosensitizer and prototype of β-carbolines, norharmane, into the cavity of cucurbit[7]uril (CB[7]) has been investigated for the first time, by using 1H NMR and UV–visible spectroscopy, and ab initio calculations.
Journal ArticleDOI
11-Aminoundecanoic acid, Cyclodextrins (α, β) and Cucurbit[n]urils (n = 6, 7) as Building Blocks for Supramolecular Assemblies: A Thermodynamic Study
TL;DR: In this paper, the formation of 1:1 complexes of α-, β-cyclodextrin, cucurbit[6]uril, and cucurbitsuril with 11-aminoundecanoic acid has been studied using calorimetric titrations.
Journal ArticleDOI
Reasons why aldehydes do not generally participate in cucurbit[n]uril forming reactions.
TL;DR: A combination of X-ray crystallography, PM3 calculations, and product resubmission experiments establish that the S-shaped isomers are thermodynamically more stable than the C-shaped diastereomers which is attributed to the conformational preferences of the newly formed benzo bicyclo[3.3.2]decane ring system.
References
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Journal ArticleDOI
I. Ueber Condensationsproducte aus Glycoluril und Formaldehyd
Journal ArticleDOI
An efficient, enantioselective synthesis of the taxol side chain
TL;DR: Synthese de la chaine du taxol a partir du phenylacetylene avec comme etapes-cle une epoxydation asymetrique et la scission regioselective de l'epoxyde as mentioned in this paper.
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A Molecular Bowl with Metal Ion as Bottom: Reversible Inclusion of Organic Molecules in Cesium Ion Complexed Cucurbituril
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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.
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Host–guest complexes of cucurbituril with the 4-methylbenzylammonium lon, alkali-metal cations and NH4+
TL;DR: In this article, the existence of two different complexes of cucurbituril with 4-methylbenzylammonium ions was reported. But the 1 : 1 stability constants were not reported for the 2 : 1 complexes with different cations.