Discover

Adamantane
Adamantane Adamantane Adamantane
General
Systematic name	Tricyclo[3.3.1.13,7]decane
Molecular formula	C10H16
SMILES	C1C2CC3CC1CC(C2)C3
Molar mass	136.23 g/mol
Appearance	White to off-white powder
CAS number	[281-23-2]
Properties
Density and phase	1.07 g/cm³ (20 °C), solid
Solubility in water	Poorly soluble
Other solvents	Soluble in hydrocarbons
Melting point	270 °C (543 K)
Boiling point	? °C (? K)
Viscosity	? cP at ? °C
Structure
Crystal structure	face-centred cubic
Dipole moment	0 D
Hazards
MSDS	External MSDS
Main hazards	Flammable
NFPA 704
Flash point
R/S statement	R: ? S: 24/25/28/37/45
RTECS number	?
Supplementary data page
Structure and properties	''n'', εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related compounds:	Memantine Rimantadine Amantadine
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

'Adamantane' (tricyclo[3.3.1.1^3,7]decane) is a colourless, crystalline compound with a camphor-like odour.^[1][2] With a formula C₁₀H₁₆, it is a cycloalkane and also the simplest diamondoid. Adamantane was discovered in petroleum in 1933.^[3] Its name derived from the Greek ''adamantinos'' (relating to steel or diamond), due to its diamond-like structure.^[4]

Contents

Synthesis

Uses

Adamantane derivatives

Adamantane analogues

References

External links

Synthesis

Adamantane was first synthesised by Prelog in 1941.^[5] A more convenient method was found by Schleyer in 1957, from dicyclopentadiene by hydrogenation followed by acid-catalysed skeletal rearrangement.^[6][7]

Uses

Adamantane itself enjoys few applications since it is merely an unfunctionalised hydrocarbon. It is used in some dry etching masks.^[8] It is also used in some polymer formulations.
In solid-state NMR spectroscopy, adamantane is a common standard for chemical shift referencing.^[9]
In dye lasers, adamantane may be used to extend the life of the gain medium; it cannot be photoionised under atmosphere because its absorption bands lie in the vacuum-ultraviolet region of the spectrum. Photoionization energies have been determined recently for adamantane as well as for several bigger diamondoids.

Adamantane derivatives

Adamantane derivatives are useful in medicine, e.g. amantadine, memantine and rimantadine. Condensed adamantanes or diamondoids have been isolated from petroleum fractions, where they occur in small amounts. These species are of interest as molecular approximations of the cubic diamond framework, terminated with C-H bonds. 1,3-Dehydroadamantane is a member of the propellane family.
Due to its stability, specific steric properties and conformational rigidity, the 1-adamantyl group is a (bulky) substituent in organic and organometallic chemistry. Some of the first persistent carbenes featured adamantyl substituents.

Adamantane analogues

Many molecules adopt cage structures with adamantanoid structures. Particularly ''useful'' compounds with this motif include P₄O₆, As₄O₆, P₄O₁₀ (= (PO)₄O₆), P₄S₁₀ (= (PS)₄S₆), and N₄(CH₂)₆.^[10]

References

1. SID 152429 -- PubChem Substance Summary
2. ADAMANTANE(TRICYCLO(3.3.1.1)DECANE)
3. , Landa, S.; Machácek, V., , , Collection Czech. Chem. Commun., 1933
4. Alexander Senning. ''Elsevier's Dictionary of Chemoetymology''. Elsevier, '2006'. ISBN 0444522395.
5. , Prelog, V., Seiwerth,R., , , Berichte, 1941
6. A Simple Preparation of Adamantane, Schleyer, P. von R., , , J. Am. Chem. Soc., 1957
7. Schleyer, P. von R.; Donaldson, M. M.; Nicholas, R. D.; Cupas, C. "Adamantane", Organic Syntheses, Coll. Vol. 5, p.16 (1973); Vol. 42, p.8 (1962).
8. RESIST COMPOSITION AND PATTERN FORMING PROCESS WATANABE, KEIJI; et al.
9. Chemical Shift referencing in MAS solid state NMR, Morcombe, C. R. and Zilm, K. W., , , J. Magn. Reson., 2003
10. Vitall, J. J., "The Chemistry of Inorganic and Organometallic Compounds with Adamantane-Like Structures", Polyhedron, 1996, 15, 1585-1642

External links