Anion Complexation by Glycocluster Thioureamethyl Cavitands: Novel ESI‐MS‐Based Methods for the Determination of K a Values

A series of saccharide‐thiourea functionalized cavitands was prepared in good yields (72–86 %) by reaction of a tetrakis(aminomethyl) cavitand with the thiocyanate derivatives of acetylated glucose, galactose, and cellobiose. The anion complexation behavior of the acetylated and deacetylated glycocl...

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Bibliographic Details
Published in:Chemistry : a European journal 2004-06, Vol.10 (11), p.2739-2748
Main Authors: Oshovsky, Gennady V., Verboom, Willem, Fokkens, Roel H., Reinhoudt, David N.
Format: Article
Language:English
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Summary:A series of saccharide‐thiourea functionalized cavitands was prepared in good yields (72–86 %) by reaction of a tetrakis(aminomethyl) cavitand with the thiocyanate derivatives of acetylated glucose, galactose, and cellobiose. The anion complexation behavior of the acetylated and deacetylated glycocluster thioureamethyl cavitands was studied with electrospray ionization mass spectrometry (ESI‐MS) in acetonitrile and in a 1:1 acetonitrile/water mixture, respectively. All compounds show a preference for Cl − . A linear relationship was found between the square root of the intensity and the concentration of the formed host–guest complex. Based on this relationship, novel methods have been developed to determine K a values, by means of direct titration and competition experiments.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200305612