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1,2-Benzoquinone

Chemical compound

Chemical compound

quinone

1,2-Benzoquinone, also called ortho-benzoquinone, is an organic compound with formula . It is one of the two isomers of quinone, the other being 1,4-benzoquinone. It is a red volatile solid that is soluble in water and diethyl ether. It is rarely encountered because of its instability, but it is of fundamental interest as the parent compound of many derivatives which are known.

Structure

The molecule has C symmetry. X-ray crystallography shows that the double bonds are localized, with alternatingly long and short C-C distances within the ring. The C=O distances of 1.21 Å are characteristic of ketones.

Preparation and reactions

1,2-Benzoquinone is produced on oxidation of catechol exposed to air in aqueous solution

A strain of the bacterium Pseudomonas mendocina metabolises benzoic acid, yielding 1,2-benzoquinone via catechol.

Ortho-quinones are widely used in organic synthesis.

Occurrence of ''ortho''-quinones

4,5-Dimethyl-1,2-benzoquinone, also a red solid, is a well behaved synthetic ortho-quinone.

The biological pigment melanin is rich in ortho-quinones.

Finally, the enzyme cofactors tryptophan tryptophylquinone (TTQ), cysteine tryptophylquinone (CTQ), lysine tyrosylquinone (LTQ) and pyrroloquinoline quinone (PQQ) contain the ortho-quinone moiety in their chemical structure.

References

ja:ベンゾキノン#1,2-ベンゾキノン

References

  1. (2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
  2. Eagleson, Mary. (1994). "Concise encyclopedia chemistry". Walter de Gruyter.
  3. (1974). "Quinonoid Compounds: Vol. 1 (1974)".
  4. (1974). "Quinonoid Compounds: Vol. 2 (1974)".
  5. (1973). "Crystal and molecular structure of o-benzoquinone". Journal of the Chemical Society, Perkin Transactions 2.
  6. (2002). "Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX)". [[Org. Lett.]].
  7. Chanda Parulekar and Suneela Mavinkurve. (2006). "Formation of ''ortho''-benzoquinone from sodium benzoate by ''Pseudomonas mendocina'' P2d". Indian Journal of Experimental Biology.
  8. (2002). "Masked o-Benzoquinones in Organic Synthesis". Accounts of Chemical Research.
  9. (1972). "Use of Dipotassium Nitrosodisulfonate (Frémy's Salt): 4,5-Dimethyl-''o''-Benzoquinone". Org. Synth..
  10. (2003). "Synthesis and Characterization of Model Compounds of the Lysine Tyrosyl Quinone Cofactor of Lysyl Oxidase". Journal of the American Chemical Society.
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