N, 



310 Uoyal Society : — 



a compound ether R" Brj or R" I^ (R" representing a bi-atomic 

 electro-positive radical) would act upon two equivalents of ammonia, 

 producing a series of salts expressed by the following formulre : — 



fR'H fR'n fR'H fR'n 



>^g:K Mflr'- Hr''K Hr''K 



LHJ LHj lhJ U"J 



In endeavouring experimentally to verify this idea, it became necessary 

 to examine what had hitherto been done in this direction. Science 

 possesses already some very interesting observations on the ammonia 

 derivatives of bi-acid alcohols. About five years ago, soon after the 

 pulilication of my experiments upon the action of ammonia upon 

 bromide and iodide of ethyle, M. Cloez* obtained a series of bases 

 on submitting ammonia to the action of the brominated Dutch liquid 

 (CjHjBro). Two of these bodies he described under the name of 

 formylia and acetylia, whilst a third body subsequently obtained is 

 designated by the term propyliaf . 



To these three bodies ^I. Cloez attributes the following formulte : — 



Formylia Cj Hg N 



Acetylia C.^ Hg N 



Propylia C, H, N. 



At a later period M. Natanson has studied the action of ammonia 

 on the chlorinated Dutch liquid (Cj H^ Clj) . This reaction produces 

 analogous results, but the number of bases is smaller, the chief 

 product being a chloride, which contains a base either identical or 

 isomeric with the acetylia of M. Cloez. 



When carefully considering the results obtained by M. Cloez, it 

 ajjpeared to me probable that the bases which he describes, are 

 in fact the di-ammoniura compounds for which I was searching. 

 The constitution assigned by M. Cloez to his substances is not very 

 probable. It is difficult to understand how the action of ammonia 

 upon a coinpound like the Dutch liquid can produce simultaneously 

 three bodies belonging to three different homologous families, the 

 formyle-, acetyle-, and propyle-series. Our doubts are, however, in- 

 creased if we examine into the physical characters of these bodies, 

 especially if we consider their high boiling temperatures, and the 

 differences between the boiling-points of the three bases : — 



Formyha. ... C, H3 N J 23° } ^iff.rence 47. 



Acetyha C, II. N 1 70°, ,.^ 



Propylia .... C„ II, N 210°} t^^ff^rence 40. 



Methylamine, C^ H- N, which contains only 2 equivalents of hy- 

 drogen more than formylia, is at the common temperature a gas, and 

 liquefies only considerably below the freezing-point of water. Again, 

 the differences of the boiling-points of substances, related in the way 

 that the formute of M. Cloez suppose, do not often exceed 20°, and 

 very rarely rise to 40° and 47°. 



All these difficulties disappear by submitting the formulae of 



M. Cloez to a shght alteration, and by regarding formylia, acetyha 



and propylia as tbe di-ammonium bases of the same series, of the 



ethylene scries. If we adopt this view, the three bodies are de- 



* Instit. 1853, 213. f Caliours, Lemons tie Cliiraie Geiicrale, t. ii. p. 054. 



