Adamantane
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.
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.
Another method involves the Meerwein's reagent in a Friedel-Crafts reaction to form adamantane from cyclohexanone.
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.
Gallery
General synthesis of adamantane
Molecular model of adamantane
Bond angles and lengths in adamantane
Numbering of carbon atoms in adamantane
Adamantane dication
Bromination of adamantane
Related pages
Adamantane
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