Summary
The acidity constants of adenosine-5′-mono- and diphosphate (AMP andADP) were determined at 25.00±0.1°C by potentiometric titration in pure water and different solvent mixtures (methanol, ethanol, N,N-dimethylformamide, dimethylsulfoxide, acetone, and dioxane). The ionization ofAMP andADP depends on both the proportion and the nature of the organic solvent used. ThepK a1 values for bothAMP andADP are slightly influenced as the solvent is enriched in ethanol and methanol and remains practically constant in presence of different amounts ofDMF andDMSO. A pronounced change in thepK a1 values is observed as the solvent is enriched in acetone or dioxane. It is concluded that the electrostatic effect has only a relatively small influence on the dissociation equilibrium, whereas other solvent effects such as solvent basicity, hydrogen bonding and protonsolvent interactions play an important role.
Zusammenfassung
Die Aciditätskonstanten von Adenosin-5′-mono- und -diphosphat wurden bei 25.0±0.1°C in reinem Wasser und in verschiedenen Lösungsmittelgemischen (Methanol, Ethanol, N,N-Dimethylformamid, Dimethylsulfoxid, Aceton und Dioxan) potentiometrisch bestimmt. Der Ionisierungsgrad vonAMP undADP hängt sowohl von der Menge als auch von der Art des organischen Lösungsmittels ab. DiepK a1-Werte vonAMP undADP werden durch Zugabe von Methanol und Ethanol nur wenig, durch verschiedene Mengen vonDMF undDMSO gar nicht, durch Aceton und Dioxan jedoch deutlich beeinflußt. Offensichtlich haben elektrostatische Effekte nur geringe Auswirkungen auf das Dissoziationsgleichgewicht, wogegen andere Faktoren wie Basizität des Lösungsmittels, Wasserstoffbrückenbindungen und Lösungsmittel-Proton-Wechselwirkungen eine bedeutende Rolle spielen.
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Azab, H.A., El-Nady, A.M. & El-Shatoury, S.A. Acidity constants of adenosine-5′-mono- and diphosphate in various water-organic solvent mixtures. Monatsh Chem 125, 1049–1057 (1994). https://doi.org/10.1007/BF00811512
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DOI: https://doi.org/10.1007/BF00811512