THE DISSOCIATION OF HEXAPHENYLETHANE FROM 
THE VIEWPOINT OF THE OCTET THEORY 
OF VALENCE 
By Howarp IRVING CoLEe 
Chemist, Bureau of Science, Manila 
HISTORICAL 
Gomberg,* in attempting to form hexaphenylethane by sub- 
jecting triphenylchlormethane to the action of metals, obtained 
a hydrocarbon possessing the requisite composition for hexa- 
phenylethane, but its remarkable activity and its unsaturated 
character presumably precluded it from actually being this com- 
pound. He expressed the opinion that this was an instance of 
a compound with one atom of carbon in the trivalent state; that 
is, triphenylmethyl (CsHs)3 = C, a free radicle. 
The original argument against the triphenylmethy] formula 
was that the determination of the molecular weight gave a dimo- 
lecular compound. This fact, however, was partly discounted 
later by the determination of the molecular weight in naph- 
thalene at elevated temperatures (79° to 80° C.), the values 
found being lower than those in other solvents. 
Markownikoff ? in 1902 held in favor of the hexaphenylethane 
formula but assumed that the latter was extremely unstable. 
He gave no reason for this instability. 
Heintschel * suggested the following formula as explaining the 
yellow color in solution: 
HH 
(cu)=c=(_ XX )=c=( GH), 
Vorlinder ‘ thought that triphenylmethyl, dimolecular, was in 
some way different from the actual hexaphenylethane, which, if 
prepared, he believed would turn out to be stable. 
*Gomberg, M., Journ. Am. Chem. Soc. 22 (1900) 757; Ber. deutsch. 
chem. Ges. 33 (1900) 8150. 
* Markownikoff, Journ. Russ. Phys. Chem. Soc. 34 (1902) 140. 
* Heintschel, E., Ber. deutsch. chem. Ges. 36 (1908) 320. 
*Vorlainder, D., Ann. = Chem. 341 (1905) 1. A 
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