Gomberg's dimer

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.

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
3D model (JSmol)
ChemSpider
PubChem CID
  • 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
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

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

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.