The electrochemical behavior and structure of silver salts of imides and carboxamides

Silver salts of amides (imides and carboxamides), containing silver cations and amidc anions in a one-to-one ratio, have been studied by electrochemical, potentiometric, and spectroscopic means.They have the structure [Amide-Ag-AmideIAg with a linear nitrogen-silver-nitrogen bond and a silver cation loosely bound to the oxygens of the amide moieties.For instance, (i) the electrochemical data show that half of the silver ions are tightly bound (morc difficult to reduce); (ii) only the loosely bound half can be titrated with chloride ions; (iii) according to 'H and "C nlnr spcctroscopy, the silver salt of succinimide ( I ) is symmetric.The selective reduction of the loosely bound silver ions in acetonitrile containing tetraethylammonium tetrafluoroborate consumes 0.5 F/mol and leads to the mixed salt [Amide-Ag-AmidcIEtrN; further reduction at a more negative potential leads to the formation of the tetraethylammonium salt, EtNAmide.' The latter two salts derived from succinimide have been prepared by a chemical route.The silver, mixed silver-tetracthylammonium, and tetraethylammonium salts are electroactive in oxidation.