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Determining the stoichiometry and binding constants of inclusion complexes formed between aromatic compounds and
Guillaume Chalumot1, Cong Yao, Verónica Pino
1Department of Chemistry, The University of Toledo, Toledo, OH 43606, USA.
Abstract:
The complexation of native beta-cyclodextrin (CD) and seven aromatic compounds, namely, phenetole, toluene, m-xylene, naphthalene, biphenyl, fluorene and phenanthrene, has been studied for first time utilizing a solid-phase microextraction (SPME)-high-performance liquid chromatography (HPLC) method. The stoichiometries of the analyte:beta-CD complexes were found to be either 1:1 or 1:2. The formation of 1:2 complexes was confirmed for naphthalene, biphenyl, fluorene, and phenanthrene only when utilizing relatively high concentrations of beta-CD (up to 6.6 mM). The 1:2 stoichiometries were confirmed using the classical modified Benesi-Hildebrand (BH) method. The calculated binding constants for 1:1 stoichiometries (K(1)) using the SPME method varied from 115.3M(-1) for toluene to 3510 M(-1) for phenanthrene, whereas the corresponding values to the 1:2 stoichiometries (K(3)) varied from 7.30 x 10(5) M(-2) for biphenyl to 9.03 x 10(6)M(-2) for naphthalene.
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