Abstract
In this research, the acid-base properties of two glycosilated flavanones namely naringoside and hesperidin were thermodynamically studied using spectrophotometric and potentiometric techniques at various temperatures (293.15–313.15) K. Because of very low solubility of these flavanones in aqueous solution, the protonation constants were obtained in ethanol-water mixtures (60–90% v/v) containing 0.10moldm−3 tetra-n-butylammonium perchlorate (TBAP) as supporting electrolyte for naringoside and DMSO-water mixed solvents (50–95% v/v) containing 0.10moldm−3 NaCl for hesperidin. Data process for the calculation of the protonation constants was done using the computer program STAR. The thermodynamic quantities (ΔG°, ΔH°, and ΔS°) of the protonation process were obtained by means of modified van't Hoff equation. It was found that the acid dissociation reaction is exothermic and the entropic contribution is low for both the flavanones. Finally, the influence of solute-solvent interactions on the protonation equilibria in various temperatures was modelled using Kamlet, Abboud and Taft (KAT) solvatochromic parameters and Hildebrand's solubility index.
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