Adamantane



Adamantane
IUPAC name Tricyclo[3.3.1.13,7]decane
Identifiers
CAS number 281-23-2
SMILES C1C2CC3CC1CC(C2)C3
Properties
Molecular formula C10H16
Molar mass 136.23 g/mol
Appearance White to off-white powder
Density 1.07 g/cm³ (20 °C), solid
Melting point

270 °C (543 K)

Solubility in water Poorly soluble
Solubility in other solvents Soluble in hydrocarbons
Structure
Crystal structure face-centred cubic
Dipole moment 0 D
Hazards
Main hazards Flammable
S-phrases 24/25/28/37/45
Related Compounds
Related compounds: Amantadine
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Adamantane (tricyclo[3.3.1.13,7]decane) is a colourless, crystalline compound with a 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] Adamantane is the most stable isomer of C10H16.

Synthesis

Adamantane was first synthesised 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 chemical shift referencing.[9]

In vacuum-ultraviolet region of the spectrum. Photoionization energies have been determined recently for adamantane as well as for several bigger diamondoids.[10]

Adamantane derivatives

Adamantane derivatives are useful in medicine, e.g. propellane family.

Due to its stability, specific steric properties and conformational rigidity, the 1-adamantyl group is a (bulky) 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), N4(CH2)6.[11]

References

  1. ^ SID 152429 -- PubChem Substance Summary. Retrieved on 14 October, 2005.
  2. ^ ADAMANTANE(TRICYCLO(3.3.1.1)DECANE). Retrieved on 14 October, 2005.
  3. ^ Landa, S.; Machácek, V. (1933). "". Collection Czech. Chem. Commun. 5: 1.
  4. ^ Alexander Senning. Elsevier's Dictionary of Chemoetymology. Elsevier, 2006. ISBN 0444522395.
  5. ^ Prelog, V., Seiwerth,R. (1941). "". Berichte 74: 1644 and 1769.
  6. ^ J. Am. Chem. Soc. 79: 3292-3292. doi:10.1021/ja01569a086.
  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. ^ ^  WATANABE, KEIJI; et al. (2001). RESIST COMPOSITION AND PATTERN FORMING PROCESS. United States Patent Application 20010006752. Bandwidth Market, Ltd. Retrieved on 14 October, 2005.
  9. ^ Corey R. Morcombe and Kurt W. Zilm (2003). "Chemical Shift referencing in MAS solid state NMR". J. Magn. Reson. 162: 479-486. doi:10.1016/S1090-7807(03)00082-X.
  10. ^ K. Lenzke, L. Landt, M. Hoener et al. (2007). "Experimental determination of the ionization potentials of the first five members of the nanodiamond series". J. Chem. Phys. 127: 084320. doi:10.1063/1.2773725.
  11. ^ Vitall, J. J., "The Chemistry of Inorganic and Organometallic Compounds with Adamantane-Like Structures", Polyhedron, 1996, 15, 1585-1642
 
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