CHEMISTRY: J. STIEGLITZ 
199 
amines, as far as the chloroamino radicle is concerned, must be a polarized 
one, R2N~+C1 and not the non-polarized union R2N^C1 permitted by 
the new theories, and that, similarly, the electronic structures of the 
alkyl and acyl chlorides should be considered polar, R3C+-CI and 
R0C+-C1. The non-polar structures RsN^Cl and RsC^Cl would not 
account at all for the persistent, fundamental differences in the proper- 
ties of the chlorine in the two series of derivatives. Now, while both 
the chloroamines and the alkyl and acyl chlorides may be minutely 
ionizable, they certainly are not electrolytes in the ordinary acceptance 
of the term. We thus find that strongly polarized combinations of 
atoms need not produce electrolytes. This being the case in an instance 
open to demonstration, one is led inevitably to the inquiry, why it 
should not be true for a great many polarized combinations and whether 
the assumption of non-polar unions is at all necessary. 
Very strong, if not so obvious, evidence, leads to the conclusion that 
the relations developed for the chloramines and the alkyl chlorides are 
duplicated by other series of compounds, for instance by the hydroxyl- 
amines^^ and the alcohols, whose relations may be expressed precisely 
and completely only in the polar structures R2N~+0H and RsC+^OH. 
Again we have no exhibition of markedly basic properties by the alco- 
hols (which form oxonium salts with acids and are 'base-forming' like 
ammonia, but not bases, ionizing directly simply as weak acids) in spite 
of the strong evidence of intramolecular ionization. 
Finally, it should be said in this connection, that exactly the same 
persistent fundamental differences as exist between positive and negative 
chlorine in organic compounds are clearly manifested between nitrogen 
as the nitrous acid radicle say in the diazo compounds^"^ and 
nitrogen as the ammonia radicle N = in the amines, amides, and nitriles. 
Here again, the relations are precisely expressed by polar structures 
for the nitrogen radicles without attendant indications of any tenden- 
cies towards ionization. 
Nothing stated in this article is, however, to be interpreted to the 
effect that one radicle may not be converted into the electromeric one 
of opposite sign; but all such transformations represent explicit, easily 
recognized oxidation-reduction reactions. 
Turning now to a further phase of this problem, we find that in the 
molecular rearrangements expressed in equations 1 and 2, the hypochlor- 
ous acid radicle of the chloroamine is converted into the common nega- 
tive chloride ion of sodium chloride. According to the original Thom- 
son theory of valence, in this change the positive chlorine atom of the 
chloroamine must capture two electrons from some other atom or atoms; 
