Date of Graduation

Summer 2009


Master of Natural and Applied Science in Chemistry


Chemistry and Biochemistry

Committee Chair

Eric Bosch


In this study I synthesized organic molecules known as ligands that selectively bind silver cations. The binding of silver to pyridine rings is well known in organometallic and coordination chemistry. The plan was to synthesize a series of new dipyridyl ligands based on 1,2-bis(2'-pyridylethynyl)benzene. To accomplish improved binding, a variety of side chains containing of oxygen, nitrogen and sulfur groups were attached to the pyridine rings. The binding constants of the ligands to silver cations were determined using 1H-NMR spectroscopy. Titrations of a silver solution into a solution containing the ligand were performed at millimolar concentrations in DMSO d-6. Following the proton shifts, we were able to calculate each ligands association constant. From the data obtained we found that the thiol containing side arm produced the highest measurable binding constant while nitrogen containing side arms yielded inconclusive results. Oxygen containing side arms were among the lowest in terms of binding constants showing that side arm in fact hindered the binding of silver to the ligand when compared to the unsubstituted bipyridyl ligand.


pyridine, ligands, silver, proton, nuclear magnetic resonance (NMR) study

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© Nathan Lael Brennan

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