Deprotonation energies of a model fulvic acid. I. Carboxylic acid groups

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Scientific paper

A model Suwannee fulvic acid (SFA [Leenheer, J.A., 1994. In: Baker, L.A. (Ed.), Chemistry of Dissolved Organic Matter in Rivers, Lakes and Reservoirs. Advances in Chemistry Series, vol. 237. American Chemical Society]) was energy minimized in various deprotonation states using semi-empirical methods. The structures were minimized in the isolated SFA phase and SFA with 60 water molecules to mimic the first solvation sphere. The relative energies of deprotonation were calculated at four carboxylic acid sites with Hartree Fock (HF/6-31G(d)) and density functional theory (B3LYP/6-31G(d)) methods. Comparisons were made between the theoretical methods and states of solvation. Isolated and solvated models resulted in different relative deprotonation orders. The energy changes calculated for removing a H+ from a given carboxylic acid group as a function of overall model molecule charge are large enough to explain the large variations of carboxyl group pKas in dissolved natural organic matter. Analysis of the SFA structure as a function of molecular charge is also discussed.

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