Numerous platinum compounds have been tested for their biological properties, however, only few are proven to be clinically useful. Palladium complexes can overcome several limitations of their platinum analogues but they are known for fast decomposition rates. We suggest that application of a fatty acid delivery system for the palladium ion will slow down the hydrolysiss rate providing desired biological properties. As a model the cyclopalladated complex of N,N-dimethylbenzylamine was chosen, where additional stabilization of the palladium center was provided by donor ligands, such as pyridine and triphenylphosphine. The fourth coordination site on palladium was varied using short-, medium-, and long-chain fatty acid carboxylates. Molecular geometries and optimization of target palladium complexes have been conducted in the aqueous solution phase using an expeditious HF/PCM model. Gibbs free energies for the first hydrolysis reaction were recorded and observed correlations are discussed. Synthesis of several candidates containing a short, a medium, and long chain fatty acids have been accomplished using solvent and solvent�free approaches. For the solvent�free methodology silica gel was used to conduct the reactions. The synthetic outcomes and efficiencies of the two approaches were compared. Purities and structures were verified using IR, 1H, and 13C NMR spectroscopies, as well as melting points. The study of antimicrobial effectiveness of obtained complexes was initiated using Gram (+) and Gram (�) bacteria and the results are compared to the obtained theoretical data.

Syntheses, thermodynamic studies, and antimicrobial properties of cyclopalladated complexes bearing fatty acid auxiliaries

248th National Meeting (2014)

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