Complexation of Methyl Orange and Tropaeolin 000 No. 2 by β-cyclodextrin dimers

Abstract

Spectrophotometric studies of the complexation of Methyl Orange (MO^-) and Tropaeolin 000 No. 2 (TR^-) anions by dimeric N,N′-bis(6^A-deoxy-6^A -β-cyclodextrin)urea (βCD)₂ur and its oxalamide and succinamide analogues, (βCD)₂ox and (βCD)₂su, respectively, are consistent with the predominant formation of complexes of the general formulae (βCD)₂x·MO^- characterized by stability constants K₁=(1.05±0.04)×10⁵, (1.92±0.04)×10⁵ and (2.50±0.02)×10⁴ dm3 mol^-1 and (βCD)₂x·TR^- characterized by K₁=(1.39±0.03)×10⁴, (7.4±0.1)×10³ and (4.60±0.05)×10³ dm3 mol^-1, in aqueous phosphate buffer at pH 9.0 and 5.5 and 298.2 K. These values are significantly greater than K₁=2160 and 710 dm3 mol^-1 for the β-cyclodextrin complexes, βCD·MO^- and βCD·TR^- and are indicative of cooperative binding in (βCD)₂x·MO^- and (βCD)₂x·TR^-. The factors affecting complex stability are discussed and comparisons are made with related systems.

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