Abstract
The influence of solvent properties on acidity constants of some newly synthesized 9,10-anthraquinone and 9-anthrone derivatives was studied in methanol-water mixtures in a composition range of 0.57 to 1.0 methanol mole fraction. The model was established by using both multiple linear regression and target factor analysis. Both methods revealed that the solvent polarity/polarizability parameter π* is a major factor in controlling the acidity behavior of the anthraquinones and anthrones studied in binary methanol-water mixed solvents. A QSPR study was conducted to drive the relationships between the π* coefficient s and the polarity/polarizability of molecules. Both dipole moment and polarizability were found to have a linear relationship with s. The results confirm that, in the dipolar protic solvents used, the dipole-dipole interaction (for neutral molecules) and the ion-dipole interaction (for ionized molecules) are the major factors controlling the acidity behavior of these compounds.
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Hemmateenejad, B., Sharghi, H., Akhond, M. et al. The Importance of Polarity/Polarizability Interaction on the Acidity Behavior of 9,10-Anthraquinone and 9-Anthrone Derivatives in Methanol-Water Mixed Solvents Using Target Factor Analysis and QSPR Approaches. Journal of Solution Chemistry 32, 215–226 (2003). https://doi.org/10.1023/A:1022982200712
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DOI: https://doi.org/10.1023/A:1022982200712