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Department of Chemistry


Department of Chemistry
Hamilton Hall
University of Nebraska
Lincoln, NE 68588-0304
Phone: (402)472-9388

 
Triarylmethyl Radical

In 1900, Moses Gomberg reported the generation of the first organic free radical, the triarylmethyl radical. The radical was formed by reacting triarylmethyl chloride with silver metal in benzene.

Gomberg Reaction

Due to its reactivity toward oxygen, Gomberg did not isolate the triarylmethyl radical, but a yellow peroxide product. Despite this problem, Gomberg confidently proposed the formation of triarylmethyl radical, a trivalent carbon species. This concept received very strong criticism; Gomberg had to be on the defense for more than 10 years.

It was Wilhelm Schlenk who provided definitive evidence for the free radical concept. Schlenk prepared tris(biphenyl)methyl radical and isolated it as black crystals. In solution, this radical was almost completely monomeric. Trisbiphenylmethyl

More on Moses Gomberg and the Triarylmethyl Radical
The Triphenylmethyl Radical
Triphenylmethyl radical : properties and synthesis
MSU Gallery of Chemists' Photo-Portraits and Mini-Biographies: Moses Gomberg
Moses Gomberg in Ann Arbor
 
References
  • Thomas T. Tidwell, "The Gomberg Century: Free Radicals 1900-2000", Advances in Physical Organic Chemistry, 2001, 36, 1-58.
  • Lennart Eberson, "Gomberg and the Nobel Prize", Advances in Physical Organic Chemistry, 2001, 36, 59-84.
  • Thomas T. Tidwell, "Wilhelm Schlenk: The Man Behind the Flask", Angew. Chem. Int. Ed., 2001, 40, 331-337
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  Created by Suchada Rajca
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  Last Updated: 7/11/04