Gomberg's dimer

Gomberg's dimer
Names
	Preferred IUPAC name 1,1′,1′′-{[4-(Diphenylmethylidene)cyclohexa-2,5-dien-1-yl]methanetriyl}tribenzene
	Other names 3-triphenylmethyl-6-diphenylmethylidene-1,4-cyclohexadiene
Identifiers
CAS Number	18909-18-7;
3D model (JSmol)	Interactive image;
ChemSpider	123721;
PubChem CID	140290;
CompTox Dashboard (EPA)	DTXSID10894912;
	InChI InChI=1S/C38H30/c1-6-16-30(17-7-1)37(31-18-8-2-9-19-31)32-26-28-36(29-27-32)38(33-20-10-3-11-21-33,34-22-12-4-13-23-34)35-24-14-5-15-25-35/h1-29,36H Key: FWSYACUVHKGULL-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)C(=C2C=CC(C=C2)C(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)C6=CC=CC=C6;
Properties
Chemical formula	C38H30
Molar mass	486.658 g·mol−1
Appearance	Yellow solid
Density	1.16 g/cm3
Melting point	140–144 °C; 284–291 °F; 413–417 K
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Gomberg's dimer is the organic compound with the formula Ph₂C=C₆H₅-CPh₃, where Ph = C₆H₅. It is a yellow solid that is air-stable for hours at room temperature and soluble in organic solvents. The compound achieved fame as the dimer of triphenylmethyl radical, which was prepared by Moses Gomberg in his quest for hexaphenylethane.

Its quinoid structure has been determined by X-ray crystallography. The C-C bond that reversibly breaks is rather long at 159.7 picometers.

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