Many metalloenzymes use polymetallic metal clusters to catalyze a wide range of chemical transformations required for life. Since such enzymes possess multiple metals in close proximity, they are capable of carrying out a variety of transformations that simple monometallic systems cannot. Consequently there is a great deal of interest in synthesizing small molecular analogs of these metalloenzymes in order to mimic their function and to learn more about how these transformations take place. Our goal is to develop new molecules (ligands) that are capable of supporting more than one metal ion. To this end, we have synthesized the novel formamidine, bis-di-2-pyridyl methyl formamidine (HBdpyF). This ligand possesses two pendent dipyridyl groups that will allow the ligand to bind two individual metal ions and bring them together thus creating a bimetallic complex.  The synthesis of HBdpyF involves three steps.  In the first step, di-2-pyridyl ketone is treated with hydroxyl amine to create an oxime.  The oxime is then reduced using Zn to form di-2-pyridyl methyl amine.  This viscous oil is reacted with triethyl orthoformate leading to the release of ethanol and formation of the desired formamidine, HBdpyF. Details of the synthesis and spectral characterization of this novel ligand will be presented.

Polypyridyl substituted formamidines: Synthesis and characterization of bis-di-2-pyridylmethyl formamidine

247th National Meeting (2014)

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