1,2-Naphthoquinone or ''ortho''-naphthoquinone is a
polycyclic aromatic
In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with formula . This yellow solid is prepared by oxidation of 1-amino-2-hydroxynaphthalene with
ferric chloride
Iron(III) chloride is the inorganic compound with the formula . Also called ferric chloride, it is a common compound of iron in the +3 oxidation state. The anhydrous compound is a crystalline solid with a melting point of 307.6 °C. The col ...
.
Occurrence
This
diketone
In organic chemistry, a dicarbonyl is a molecule containing two carbonyl () groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls ...
(an ortho-
quinone) is a metabolite of
naphthalene. It arises from the
naphthalene-1,2-oxide.
It is also found in diesel exhaust particles. The accumulation of this toxic metabolite in rats from doses of naphthalene has been shown to cause eye damage, including the formation of
cataract
A cataract is a cloudy area in the lens of the eye that leads to a decrease in vision. Cataracts often develop slowly and can affect one or both eyes. Symptoms may include faded colors, blurry or double vision, halos around light, trouble ...
s.
See also
*
1,4-Naphthoquinone, an
isomer of 1,2-naphthoquinone
References
External links
*
*
{{DEFAULTSORT:Naphthoquinone, 1, 2-
1,2-Naphthoquinones