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.° 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;C—X possess the tendency to tautomerize to the quinoid 
modification: 
(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: 
_ / CH, 
H 
C,H 
“San, Pipa wre 
C( C,H,), C==(C,4), 
Gomberg now suggested an explanation which embraces all 
of the factors concerned: (1) the unsaturated character of tri- 
phenylmethy]; (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: 
I. (R,C ),,( associated molecule) 
eae H 
u.| Rc" a sae | 
It H 
WW. + p68 x pon 
Ty. R,C—CR;( Hexaphenylethane ) 
” Journ. Am. Chem. Soc. 35 (1913) 1035. 
