II. CHEMISTRY 13 



periodate, enneaiodide, phosphotungstate, phosphomolybdate, reineckate, 

 and salts with Mayer's reagent (potassium mercuric iodide) and with 

 lu'aut's reagent (potassium bismuth iodide). The chloroplatinate is mod- 

 erately soluble in water but very insoluble in ethanol. The flavianate is 

 sparingly soluble in ethanol and is insoluble in N-butanol. 



The properties of some of the more important salts are listed below: 



Chloride (C5H14ONCI): Soluble in water, methanol, ethanol, and formal- 

 dehyde; less soluble in carbon tetrachloride, chloroform, and acetone; 

 insoluble in carbon disulfide, benzene, toluene, ether, and petroleum ether; 

 deliquescent; stable up to 180°, decomposing on heating to give dimethyl- 

 aminoethanol and methyl chloride. 



Reineckate (Ci5H,40N-C4H7N6S.Cr): Melts above 2m°f soluble in 

 water at 18° up to 0.02 %, in 10 % hydrochloric acid up to 0.03 %; in the 

 presence of excess ammonium reineckate the solubility in water is greatly 

 depressed ;^^ insoluble in dilute ammonia, 0.1 TV sodium hydroxide, ethanol, 

 benzene, and ether, but has an appreciable solubility in acetone. ^^' ^^ 



Periodides: Periodides of choline are precipitated by iodine in potassium 

 iodide solution, either as an insoluble oil or as a crystalline material, de- 

 pending upon the conditions.^^' ^^ 



Hexaiodide (CsH^ON-I-Is): Black greenish iridescent oil obtained when 

 potassium triiodide solution is added to an excess of choline chloride; very 

 insoluble in water and soluble in ethanol; converted to the enneaiodide by 

 treatment mth KI3 solution or powdered iodine. 



Enneaiodide (CsHuON • I • Ig) : Green needles, soluble in alcohol but very 

 insoluble in water; loses iodine rapidly in air and goes over to the hexa- 

 iodide. 



Mercuric chloride double salt (CsHhON-CI-G HgCl2): Melts at 249 to 

 251°,^^ 242 to 243°;^" insoluble in cold water and very insoluble in alcohol. 



Chloroaurate (CsHhON-CI-AuCIs): Melts at 243 to 244° (slow heating), 

 259° (rapid heating),^^ 257°9« 267 to 210° f deep yellow needles from hot 

 alcohol or octahedra and cubes from dilute alcohol; sparingly soluble in 

 water, and very insoluble in alcohol. 



Chloroplatinate (C5Hi40N-Cl)2PtCl4: Quickly decomposes on heating at 

 241 to 242°;®^ dimorphous; crystallizes in cubes and octahedra from hot 

 alcohol and water (1:1), but in six-sided pyramids or monoclinic rhombic 



83 G. Bischoff, W. Grab, and J. Kapfhammer, Huppe-Seyler's Z. physiol. Chem. 200, 



153 (1931). 

 '■* E. Strack and H. Schwaneberg, Hoppe-Seyler's Z. physiol. Chem. 245, 11 (1936). 

 96 H. Paal, Biochem. Z. 211, 244 (1929). 

 86 F. H. Shaw, Biochem. J. 32, 1002 (1938). 



8' J. Smorodinzew, Hoppe-Seyler's Z. physiol. Chem. 80, 218 (1912). 

 98 C. Reuter, Hoppe-Seyler's Z. physiol. Chem. 78, 167 (1912). 



