Acenaphthoquinone

Acenaphthoquinone is a type of quinone, a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds", resulting in "a fully conjugated cyclic dione structure". Acenaphthoquinone is a yellow crystalline solid and is considered to be a derivative of acenaphthene.

Structure and Properties

Acenaphthoquinone is a polycyclic aromatic hydrocarbon (PAH) with the molecular formula C12H6O2. It consists of a naphthalene core with two carbonyl groups (C=O) at the 1 and 2 positions. The structure of acenaphthoquinone is planar, which is typical for PAHs.

The compound is a yellow crystalline solid at room temperature. It is slightly soluble in water, but more soluble in organic solvents such as ethanol and diethyl ether.

Synthesis

Acenaphthoquinone can be synthesized from acenaphthene via oxidation. This can be achieved using a variety of oxidizing agents, such as chromic acid or potassium permanganate.

Applications

Acenaphthoquinone is used as a starting material in the synthesis of various dyes and pharmaceuticals. It is also used in the production of certain types of plastics and resins.

Safety

Like many PAHs, acenaphthoquinone is considered to be potentially hazardous. It can cause skin and eye irritation, and prolonged exposure can lead to more serious health effects.

See Also

• Quinone
• Acenaphthene
• Polycyclic aromatic hydrocarbon