68 
CHEMISTRY: E. C. FRANKLIN 
METALLIC SALTS OF AMMONO ACIDS 
By Edward C. Franklin 
DEPARTMENT OF CHEMISTRY. STANFORD UNIVERSITY 
Presented to the Academy, January 9, 1915 
The Action of Liquid-Ammonia Solutions of Ammono Acids on Metallic 
Amides, Imides, and Nitrides. The acid amides and imides, and the 
metallic derivatives of the acid amides and imides are the acids, bases, 
and salts respectively of an ammonia system of acids, bases, and salts. ^ 
Guided by the relationships implied in the above statement Franklin 
and Stafford were able to prepare potassium derivatives of a considerable 
number of acid amides by the action of potassium amide on certain acid 
amides in solution in liquid ammonia. That is to say, an ammono 
base, potassium amide, was found to react with ammono acids in liquid 
ammonia to form ammono salts just as the aquo base, potassium hydrox- 
ide, acts upon aquo acids in water solution to form aquo salts. Choos- 
ing, for example, benzamide and benzoic acid as representative acids 
of the two systems, the analogous reactions taking place respectively 
in liquid ammonia and water are represented by the equations : 
C6H5CONH2+KNH2 = C6H5CONHK -f NH3. 
C6H5CONH2 + 2KNH2 = C6H5CONK2 + 2NH3. 
CeHsCOOH -f KOH = CeHsCOOK + H2O. 
The ammono acid, since it is dibasic, reacts with either one or two 
molecules of potassium amide to form an acid and a neutral salt. 
Having thus demonstrated the possibility of preparing ammono salts 
of potassium by the interaction of potassium amide and acid amides 
in liquid ammonia solution, it was further found that ammono salts of 
the heavy metals may be prepared by the action of liquid ammonia 
solutions of ammono acids on insoluble metallic amides, imides, and 
nitrides — that is, by reactions which are analogous to the formation of 
aquo salts in water by the action of potassium hydroxide on insoluble 
metallic hydroxides and oxides. 
In the present investigation the action of acetamide, benzenesulfon- 
amide, and paratoluenesulfonamide on the amide of silver, on the imides 
of copper and lead, and on the nitride of thallium has been studied. 
The method for the preparation of a typical compound may be briefly 
described. Pure silver amide, prepared in a two-legged reaction- tube^ 
by thoroughly washing the precipitate resulting from the interaction of 
potassium amide and silver nitrate in liquid-ammonia solution, is dis- 
