Anion Binding Properties of 2,3-O-Dibenzyl-α- and β-Cyclodextrin Derivatives

Title:Anion Binding Properties of 2,3-O-Dibenzyl-α- and β-Cyclodextrin Derivatives

Volume: 11 Issue: 10

Author(s): Nobuyuki Karube and Kazuaki Ito

Affiliation:

Keywords: Acetate, anion receptor, cyclodextrin, dihydrogen phosphate, hydrogen bonding, hydroxyl group.

Abstract: Cyclodextrins (CDs) have been investigated as scaffolds for the construction of anion receptors. Modified α- and β-CDs (1a and 1b, respectively), where hydroxyls on C-2 and C-3 are protected by benzyl groups have been synthesized, and their anion binding properties in CD₃CN as an anion receptor were investigated by ¹H-NMR titration experiments. CD-based receptors (1a and 1b) effectively bind with AcO^- and H₂PO₄ ^- by cooperative intermolecular hydrogen bonds with alcoholic hydroxyl groups on C-6. The trends in selectivity can be rationalized on the basicity of the anions and the size of the binding pocket in the receptor.

Cite this article as:

Karube Nobuyuki and Ito Kazuaki, Anion Binding Properties of 2,3-O-Dibenzyl-α- and β-Cyclodextrin Derivatives, Letters in Organic Chemistry 2014; 11 (10) . https://dx.doi.org/10.2174/157017861110141117121751