Adamantane

Adamantane

File:Adamantane acsv.svg

Structural formula of adamantane

Adamantane is a chemical compound with the formula C__H__. It is a colorless, crystalline substance with a camphor-like odor. Adamantane is the simplest diamondoid, a class of hydrocarbons that resemble the diamond lattice structure.

Structure

Adamantane is a tricyclic saturated hydrocarbon with a unique cage-like structure. It consists of three fused cyclohexane rings in a chair conformation, forming a rigid, symmetrical framework. This structure is responsible for its high melting point and stability.

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Crystals of adamantane

Synthesis

Adamantane can be synthesized through several methods. One of the earliest methods was developed by Vladimir Prelog in 1941, involving the hydrogenation of dicyclopentadiene.

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Synthesis of adamantane by Prelog

Another method involves the Meerwein's reagent in a Friedel-Crafts reaction to form adamantane from cyclohexanone.

File:Meerweins Ether.png

Meerwein's ether used in synthesis

Properties

Adamantane is known for its high thermal stability and resistance to chemical reactions. It has a melting point of 270 °C and is soluble in nonpolar solvents such as benzene and carbon tetrachloride.

Applications

Adamantane and its derivatives have applications in pharmaceuticals, polymers, and nanotechnology. Derivatives such as amantadine are used as antiviral drugs and in the treatment of Parkinson's disease.

Derivatives

Adamantane can be functionalized to form a variety of derivatives, including adamantanone, bromoadamantane, and adamantylamine. These derivatives are used in various chemical and pharmaceutical applications.

File:Adamantanone synthesis.png

Synthesis of adamantanone

Gallery

• General synthesis of adamantane
  General synthesis of adamantane
• Molecular model of adamantane
  Molecular model of adamantane
• Bond angles and lengths in adamantane
  Bond angles and lengths in adamantane
• Numbering of carbon atoms in adamantane
  Numbering of carbon atoms in adamantane
• Adamantane dication
  Adamantane dication
• Bromination of adamantane
  Bromination of adamantane

Related pages

• Diamondoid
• Cyclohexane
• Amantadine
• Hydrocarbon

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