Inclusion complexes of bisphenol A with cyclomaltoheptaose (beta-cyclodextrin): solubilization and structure.
The inclusion complexation behavior and the solubilization effects of Bisphenol A (BPA, an endocrine-disrupting chemical) by cyclomaltohexaose, -heptaose, and -octaose (alpha-, beta-, and gamma-cyclodextrins) were investigated by (1)H NMR spectroscopy and by elemental analysis. The results showed that beta- and gamma-cyclodextrins gave the satisfactory solubilization ability to BPA up to 7.2 x 10(3) mg L(-1) and 9.0 x 10(3) mg L(-1), respectively. X-ray crystallographic diffraction and ROESY spectroscopy were also employed to investigate the structure of the beta-CD/BPA inclusion complex in both aqueous solution and the solid state. The result showed that this complex adopted a 2:2 stoichiometry in the solid state, that is, a head-to-head beta-CD dimer accommodated two BPA molecules. The inclusion of BPA led to the desolvation of the beta-CD cavity and the destruction of the circularly closed hydrogen-bond network in the secondary side of beta-CD, which made the complex more soluble.
Yang
Zi-Xin
ZX
Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
Chen
Yong
Y
Liu
Yu
Y
D001559:Benzhydryl Compounds; D002236:Carbohydrate Conformation; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010636:Phenols / Q000737:chemistry*; D012995:Solubility; D014867:Water / Q000737:chemistry; D047392:beta-Cyclodextrins / Q000737:chemistry*; D000098826:Bisphenol A Compounds
D001559:Benzhydryl Compounds; D010636:Phenols; D014867:Water; D047392:beta-Cyclodextrins; C031215:betadex; C006780:bisphenol A; D000098826:Bisphenol A Compounds