The Effect of Aromatic Tertiary Amines on the Copper(II) Catalyzed Decarboxylation of 3-Oxo-Glutaric Acid

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Abstract
The kinetics of the copper(II) catalyzed decarboxylation of 3-oxo-glutaric acid have been investigated in unbuffered solutions at 25 °C and 0.60 M ionic strength, both in the presence of aromatic tertiary amines, and with hydrated copper ions alone. The amines used were 2,2′-bipyridyl and 1,10-phenanthroline. Equilibrium constants for the formation of the various copper complexes were determined with a copper ion selective electrode, particularly for the species CuAB, where A is the 3-oxo-glutarate ion, and B is an aromatic amine. The kinetic behavior was then interpreted as arising from the simultaneous decarboxylation of all the species present containing a 3-oxo-glutarate ligand. The resulting rate constants indicated that some kinetic effect was transmitted through the copper from the base to the 3-oxo-glutarate, but the effect was relatively small, and the bulk of the catalytic effect caused by the base arose from changes in equilibrium concentrations.

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