CHEMISTRY: J. STIEGLITZ 
20! 
that we may have non-polar, as well as polar valences existing simultan- 
eously in molecules, we find the following: (1) It is necessary to assume 
polar valences in the chloroamine radicle, as was proved above. (2) 
We recognize the positively polarized chlorine as the unstable element 
in the molecule. (3) In the product, phenylimido benzophenone, we 
must assume at least partial polarization of the methylene carbon and 
nitrogen, in order to express precisely its mode of hydrolysis (equation 
4). (4) It is necessary to assume therefore that at least one electron 
has migrated from the methyl carbon to the nitrogen (or chlorine). 
(5) To these definite conclusions may be added the fact that a pre- 
sumptively negative group ~0R attached to carbon never migrates^^ to 
nitrogen under these conditions, it is only presumably positive alkyl 
(CH3+) or alphyl (CeHs^) radicles and hydrogen radicles H+ that mi- 
grate thus. In other words, so far as experiment penetrates into these 
molecular rearrangements, we find in the original molecule, in the reac- 
tion itself and in the product of the rearrangement evidences only of 
polar valences. The later modifications of the Thomson theory are of 
no assistance in formulating the theory of these reactions. 
Finally, there is a whole group of rearrangements analogous to the 
rearrangement of chloroamines. In each instance one can plainly rec- 
ognize, as the common characteristic of all the rearranging compounds, 
that the labile component in the original molecule is an unstable positive 
radicle or atom, which tends to go over into its stable negative form. 
In every instance, this tendency is found satisfied in the action, and as 
this involves the absorption of electrons from neighboring atoms in the 
original molecule, one must conclude that in all of these cases the tend- 
ency mentioned and its satisfaction bring about the rearrangement. 
These relations hold for the following groups of compounds: 
1. Hydroxylamine dmYdutiYQS, such dj^ (C6H5)3C.HN~+OH (considered 
in the following article), in which the positive hydroxide group^^ is un- 
stable, tending to form the well known negative group. The molecular 
rearrangement may be expressed^^ by the same equation 3 as was used 
for the chloroamine, if +0H is substituted for C1+ and H0~ for Cl~. 
;;n:i 
2. Azides, s^uch. {C^t)z^^^ N=:<' li (see the following article), 
which tend to lose the neutral molecule N2 with a gain of two electrons 
for the radicle Again equation 3 may be used to express the whole 
action, the loss of N2 being substituted for the loss of HCl. (The azide 
is formed by the action of nitrous acid N^jl'^IO ("OH) on the hydra- 
zine (C6H5)3C.HN - + NH2,i^ which leads to the structure used. 
