196 
CHEMISTRY: J. STIEGLITZ 
indicated by Dimroth's reasoning, although no evidence of a direct 
nature was adduced and only the reactions of the mercury were 
considered in assigning the formula. It seemed to the writers that a 
study of the amino group in these compounds would furnish more direct 
evidence as to the structure than any at hand, for, obviously, a com- 
pound of the formula (I), where R = H, could not undergo the reac- 
tions characteristic of the primary amino group. This work was there- 
fore undertaken as a preliminary phase of a more extended study of 
the mercuriated aromatic amines. It was found possible to prove 
formula (II) for ^-aminophenylmercuric acetate by demonstrating the 
presence of the primary amino group in two ways: (1) the formation 
of a saHcylidene derivative; (2) the ready formation of a diazo solution, 
from which were prepared the azo dyes with dimethylaniHne, diethyl- 
aniHne, phenol, resorcin, and a-naph thy lamine-5 -sulfonic acid. It was 
also found possible to prove the monomolecular structure of ^-methyl- 
aminophenylmercuric acetate by demonstrating the presence of a sec- 
ondary amino group through the preparation of the nitroso derivative. 
A more detailed discussion and a description of the compounds prepared 
will appear in the Journal of Biological Chemistry. 
^Zs. anorg. Chem., 32, 227 (1902). 
^Berlin, Ber. D. hem. Ges., 35, 2038 (1902); Zs. anorg. Chem., 33, 311 (1902). 
MOLECULAR REARRANGEMENTS OF TRIPHENYLMETHANE 
DERIVATIVES. I. GENERAL DISCUSSION 
By Julius Stieglitz 
KENT CHEMICAL LABORATORY. UNIVERSITY OF CHICAGO 
Read before the Academy, December 9. 1914. Received, February 20, 1 9 1 5 
Introduction. — In most chemical actions taking place at moderate 
temperatures, a change affecting an atom or a group of atoms in a 
molecule leaves the remaining atoms in undisturbed relations to one 
another. This stability of groupings of atoms led, especially in the 
domain of organic chemistry, to the theory of the structure of molecules 
and underlies our methods for determining these structures. Occasion- 
ally, however, the study of the product of a reaction shows that a pro- 
found rearrangement of the grouping of atoms in a reacting molecule 
has taken place. Molecular rearrangements of this kind are of special 
interest for the reason that their study should shed some light, from a 
purely chemical side, on the forces holding atoms in place in molecular 
structures. The evidence thus obtained should aid in the study of 
these forces by purely physical means. 
