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1 Polish Journal of Chemistry

1 1998

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The stoichiometry and stability of beta-cyclodextrin complexes of some aromatic ketones and thioketones

Milewski M., Urjasz W., Maciejewski A., Augustyniak W.

Polish Journal of Chemistry

1998

Vol. 72, nr 11

2405-2417

Stoichiometry and stability constants of beta-cyclodextrin (beta-CD) complexes of several aromatic ketones and the corresponding thioketones were determined by the spectrophotometric and solubility methods. The solubility method with high-performance liquid chromatography (HPLC) detection of the solute concentration proved to be very convenient in determination of the stability constant for the least soluble thioketone. The formation constants were correlated with 1-octanol-water partition cefficients, which vary over more than five orders of magnitude for compounds studied. The hydrophobic interaction and dispersion forces were found to be the most important sources of the complex stability. Relatively strong hydrogen bonds between the ketone molecules and water destabilize their beta-cyclodextrin complexes. Stoichiometry of all beta-cyclodextrin complexes studied was found to be 1:1. The synthesis of a new alkyl derivative of 4H-1-benzopyran-4-one and 4H-1-beznopyran-4-thione was described.