Abstract: Acetonitrile is a simple organic molecule and is often used as a reaction solvent. But can acetonitrile and other nitriles be used as inexpensive building blocks for pharmaceutical and agricultural products? In the Turlington lab, we investigate the reactivity of nitriles when they are coordinated to transition metals. Based on the well-known field of nitrile hydrolysis, where water performs a nucleophilic attack on a metal-coordinated nitrile ligand to form an amide, we wondered what would happen instead if a chemical oxidant could be enticed to do a nucleophilic attack and then an oxidation of an acetonitrile ligand. We postulated that this could be a new avenue to generate reactive metal-imido intermediates, and metal-imido intermediates are known to be reactive species of many carbon-nitrogen bond forming reactions, making products such as aziridines. We have synthesized ruthenium(II)nitrile compounds and will report their reactivity when oxidized. Data from 1H and 13C NMR spectra will be presented that show evidence of oxidants reacting with coordinated nitrile ligands, and the products of the reaction suggest that reactive metal-imido intermediates were generated in situ.
Originally published at chemistry.nd.edu.