19,6 Cole: Dissociation of Hexaphenylethane 683 
Later a number of the carbinols themselves were found ca- 
pable of existing in the quinoid state as well as in the benzenoid 
state. 10 These and other experiments led Gomberg to conclude 
that (1) triphenylmethyl in solution behaves as if it had the 
quinol structure, either as a temporary base or as one in equili- 
brium with some other phase; (2) compounds of the type 
R 3 C— X possess the tendency to tautomerize to the quinoid 
modification : 
H 
(3) since the nature of the group X may apparently vary 
within wide limits then, as a corollary to the second conclusion, 
it follows that hexaphenylethane, considered as a triphenylme- 
thane derivative, may also possess the tendency to tautomerize 
and give rise to a compound of quinol composition : 
H 
(C,H > ), = C = <f~Y 
C = (C 6 H s )j 
•C 6 H 5 
■c s h 5 
•C(CH 
5' 3 
Gomberg now suggested an explanation which embraces all 
of the factors concerned: (1) the unsaturated character of tri- 
phenylmethyl; (2) the existence of the two, colorless and colored, 
modifications; (3) the dimolecular state in solution; (4) the 
probability of the quinollike structure; (5) the possible exist- 
ence of an unstable hexaphenylethane: 
R S C ) n ( associated molecule) 
n. 
w. 
R 3 C — C R 3 ( Hexaphenylethane) 
“Journ. Am. Chem. Soc. 35 (1913) 1035. 
