Controlling Factors in the Synthesis of Cucurbituril and Its Homologues
Top Cited Papers
- 1 November 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (24) , 8094-8100
- https://doi.org/10.1021/jo015897c
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.Keywords
This publication has 13 references indexed in Scilit:
- Effects of Alkali and Alkaline-earth Cations on the Removal of Reactive Dyes with CucurbiturilActa Hydrochimica et Hydrobiologica, 1999
- HPLC Analysis of the Products of the Reaction Between Glycoluril and FormaldehydeJournal of Liquid Chromatography & Related Technologies, 1998
- The formation of cucurbituril complexes with amino acids and amino alcohols in aqueous formic acid studied by calorimetric titrationsThermochimica Acta, 1998
- Thermal behaviour of hydrated and anhydrous Cucurbituril: A DSC, T.G. and calorimetric study in temperature range from 100 to 800KThermochimica Acta, 1998
- Complexes of cucurbituril with alkyl mono- and diammonium ions in aqueous formic acid studied by calorimetric titrationsThermochimica Acta, 1997
- Cucurbituril: Supramolecular perspectives for an old ligandJournal of inclusion phenomena and molecular recognition in chemistry, 1994
- Host–guest complexes of cucurbituril with the 4-methylbenzylammonium lon, alkali-metal cations and NH4+Journal of the Chemical Society, Faraday Transactions, 1994
- Decamethylcucurbit[5]urilAngewandte Chemie International Edition in English, 1992
- An efficient, enantioselective synthesis of the taxol side chainThe Journal of Organic Chemistry, 1986
- I. Ueber Condensationsproducte aus Glycoluril und FormaldehydEuropean Journal of Organic Chemistry, 1905