(Thio)Urea-Functionalized Cavitands as Excellent Receptors for Organic Anions in Polar Media

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Title:(Thio)Urea-Functionalized Cavitands as Excellent Receptors for Organic Anions in Polar Media
Creators:
Oshovsky, Gennady V.
Verboom, Willem
Reinhoudt, David N.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 5, pp. 1137-1148
Uncontrolled Keywords:Cavitands, Binding constants, Receptors, Recognition, Microcalorimetry, Anions, Glycosides, Carboxylates

Abstract

Ureidocavitand <strong>1</strong> and thioureidocavitand <strong>2</strong> bind in CH<sub>3</sub>CN organic anions such as acetate, propionate, butyrate, etc. with <i>K</i> values of 2-8 × 10<sup>5</sup> l mol<sup>-1</sup> and 2-9 × 10<sup>6</sup> l mol<sup>-1</sup>, respectively, as was determined with isothermal microcalorimetry (ITC). Bringing together four (thio)urea binding sites on a molecular platform gives rise to about 2000 times higher binding constants, compared with those of the corresponding single binding sites. Glucose- and galactose-containing thioureidocavitands <strong>5</strong> and <strong>6</strong> bind acetate in 1:1 CH<sub>3</sub>CN/water with a <i>K</i>-value of 2.15 × 10<sup>3</sup> l mol<sup>-1</sup>. <p>

Title:(Thio)Urea-Functionalized Cavitands as Excellent Receptors for Organic Anions in Polar Media
Creators:
Oshovsky, Gennady V.
Verboom, Willem
Reinhoudt, David N.
Uncontrolled Keywords:Cavitands, Binding constants, Receptors, Recognition, Microcalorimetry, Anions, Glycosides, Carboxylates
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:69
Number:5
Page Range:pp. 1137-1148
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20041137UNSPECIFIED
ID Code:2266
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Oshovsky, Gennady V.; Verboom, Willem; Reinhoudt, David N. (2004) (Thio)Urea-Functionalized Cavitands as Excellent Receptors for Organic Anions in Polar Media. Collection of Czechoslovak Chemical Communications, 69 (5). pp. 1137-1148. ISSN 0010-0765

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