TRuVNSACTlONS OF THE SECTIONS. 43 



Thiis, iu tlie famous process for producing aniline blue three atoms of phenyl are 

 changed against three atoms of hydrogen, 



C,„H^,N3+3C„H,H,N=C,„H,,(3CJl3)N3+8H3K* 



Hofmanu's beautiful research relatiug to this transformation of aniline red into 

 aniline blue leaves no doubt that three atoms of hydrogen are concerned. 



Again, the iodides of the alcohol radicrds react upon rosauiline, producing 

 ethylated bases. Hofmann has not yet published his research on "Ethyl-rosa- 

 niline," but, judging from the quantity of iodide of ethyl actually destroyed iu the 

 operation, there can be little doubt tliat substitution goes on to the length of three 

 atoms. 



In order to judge whether this action upon the " hydrogen atoms " in rosauiline 

 must be looked upon as a very close representation of the action upon the hydrogen 

 atoms in common ammonia, 1 have inquired whether Cai'ey Lea's method 'was ap- 

 plicable to rosauiline. 



Carey Lea, as is well known, has sho-\vn that nitrate of ethyl occupies a place 

 among the very few ethers capable of forming ethylated ammonias by reaction upon 

 ammonia. I have recently succeeded in obtaining ethylated rosauiline by the action 

 of nitrate of ethyl upon rosauiline. 



From all this it results that the rational formula of rosauiline must display three 

 atoms of hydrogen in association with nitrogen. 



A consideration of the entire case leads me to propose the following formula : — 



Tvpe. 



fNHCeH, VH 



pjNHC.H, ^Jh 



•"^iNIIC.H, ^n H 



Lh Lh 



I here wi-ite rosanUine on the " ethylene" tj'pe, replacing three atoms of typical 

 hydrogen by three atoms of phenylamid. 



Just as ethylene tends to take up the representatives of two atoms of hydi-ogen, 

 and thereby passes into a body of the "hydride of ethyl" type, so rosauiline tends 

 to take up two atoms of hydrogen, thereby becoming a representative of hydride of 

 ethyl. 



[h H 



H |H 



ll 



II 



Eosaniline. Leucaniline. 



fNHC.H- 



I'NHC.H, INHcIh! 



(.JNHC.H „_„ 



^^'INHC" H +^-*"* 



LH 



NHC.H, 



H 



H 



H 



The three atoms of hydrogen in union with the three atoms of nitrogen are, of course 

 easily replaceable. ° ' 



The fourth atom of hydrogen, being in direct association with carbon, is not easily 

 replaceable. 



The power that nitrogen has of being either three or five atomic is, of course, the 

 explanation of the mono-acid and tri-acid salts. There should be Uiewise bi-acid 

 salts. 



* The first suggestion of the kind of change which takes place when aniline red becomes 

 aniline blue was, I behave, due to me. In the winter of 1862-63 I explained it by saying 

 that anUine red lost hydrofrm and gained phenyl ; supporting my view by adducing the 

 faot that the red gave more than its weight of blue while ammonia' was evolved. 



