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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
Dimer may refer to:
* Dimer (chemistry), a chemical structure formed from two similar sub-units
** Protein dimer, a protein quaternary structure
** d-dimer
* Dimer model, an item in statistical mechanics, based on ''domino tiling''
* Julius Dimer ...
of triphenylmethyl radical
The triphenylmethyl radical (often shorted to trityl radical) is an organic compound with the formula (C6H5)3C. It is a persistent radical. It was the first radical ever to be described in organic chemistry. Because of its accessibility, the tri ...
, which was prepared by Moses Gomberg
Moses Gomberg (February 8, 1866 – February 12, 1947) was a chemistry professor at the University of Michigan. He was elected to the National Academy of Sciences and served as president of the American Chemical Society.
Early life and education
...
in his quest for hexaphenylethane
Hexaphenylethane is a hypothetical organic compound consisting of an ethane core with six phenyl substituents. All attempts at its synthesis have been unsuccessful. The trityl free radical, Ph3C, was originally thought to dimerize to form hex ...
.
Its quinoid
In organic chemistry, quinoids are a class of chemical compounds that are derived from quinone. Unlike benzenoid structures, the quinoid part is not aromatic.
See also
* Benzenoid
In organic chemistry, benzenoids are a class of organic compou ...
structure has been determined by X-ray crystallography
X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles ...
. The C-C bond that reversibly breaks is rather long at 159.7 picometer
The picometre (international spelling as used by the International Bureau of Weights and Measures; SI symbol: pm) or picometer (American spelling) is a unit of length in the International System of Units (SI), equal to , or one trillionth of ...
s.
Synthesis and reactions
Gomberg's dimer can be prepared quantitatively by treating trityl bromide with powdered copper or silver: :2Ph3CBr + 2Cu → Ph2C=C6H5-CPh3 + 2CuBr Gomberg's dimer reversibly dissociates to thetriphenylmethyl radical
The triphenylmethyl radical (often shorted to trityl radical) is an organic compound with the formula (C6H5)3C. It is a persistent radical. It was the first radical ever to be described in organic chemistry. Because of its accessibility, the tri ...
in organic solvents:
:
See also
*Hexaphenylethane
Hexaphenylethane is a hypothetical organic compound consisting of an ethane core with six phenyl substituents. All attempts at its synthesis have been unsuccessful. The trityl free radical, Ph3C, was originally thought to dimerize to form hex ...
References
{{reflist Aromatic hydrocarbons