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Adamantane
Adamantane
Adamantane
Adamantane
IUPAC name
Other names Tricyclo[3.3.1.13,7]decane
Identifiers
CAS number 281-23-2 Yes check.svgY
PubChem 9238
SMILES
InChI
InChI key ORILYTVJVMAKLC-UHFFFAOYAG
ChemSpider ID 8883
Properties
Molecular formula C10H16
Molar mass 136.23 g mol−1
Appearance White to off-white powder
Density 1.07 g/cm³ (20 °C), solid
Melting point

270 °C (543 K)

Boiling point

Sublimes

Solubility in water Poorly soluble
Solubility in other solvents Soluble in hydrocarbons
Structure
Crystal structure cubic Space group Fm3m
Coordination
geometry
4
Dipole moment 0 D
Hazards
S-phrases 24/25/28/37/45
Related compounds
Related compounds: Memantine
Rimantadine
Amantadine
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Adamantane (tricyclo[3.3.1.13,7]decane) is a colourless, crystalline compound with a camphor-like odour.[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]

Adamantane is the most stable among all the isomers with formula C10H16, which include the somewhat similar twistane.

Contents

Synthesis

Adamantane was first synthesised by Prelog in 1941.[5][6] A more convenient method was found by Schleyer in 1957, from dicyclopentadiene by hydrogenation followed by acid-catalysed skeletal rearrangement.[7][8]

Adamantane synthesis.png

Properties

At ambient conditions, admanatane crystallizes in a cubic structure containing orientationally disordered adamantane molecules. This structure transforms into an ordered tetragonal phase with two molecules per cell either by cooling to 208 K or by pressurizing above 0.5 GPa. In both phases, the adamantane molecules are not cubic, but ellipsoidally distorted. However, the carbon-carbon distances 1.53 A are close to that in diamond (1.54 A). Adamantane is volatile and sublimes even at room temperature.[9]

Uses

Adamantane itself enjoys few applications since it is merely an unfunctionalised hydrocarbon. It is used in some dry etching masks.[10] It is also used in some polymer formulations.

In solid-state NMR spectroscopy, adamantane is a common standard for chemical shift referencing.[11]

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.[12]

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 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 phosphorus trioxide P4O6, arsenic trioxide As4O6, phosphorus pentoxide P4O10 = (PO)4O6, phosphorus pentasulfide P4S10 = (PS)4S6, and hexamethylenetetramine C6N4H12 = N4(CH2)6.[13] Particularly notorious is Tetramethylenedisulfotetramine, often shortened to "tetramine", a rodenticide banned in most countries for extreme toxicity to humans.

References

  1. ^ According to page 41 of a 2004 IUPAC guide, adamantane is the "preferred IUPAC name."
  2. ^ "ADAMANTANE(TRICYCLO(3.3.1.1)DECANE)". http://www.chemicalland21.com/arokorhi/lifescience/phar/ADAMANTANE.htm. Retrieved 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). "Über die Synthese des Adamantans". Berichte 74: 1644–1648. doi:10.1002/cber.19410741004.  
  6. ^ Prelog, V., Seiwerth,R. (1941). "Über eine neue, ergiebigere Darstellung des Adamantans". Berichte 74: 1769–1772. doi:10.1002/cber.19410741109.  
  7. ^ Schleyer, P. von R. (1957). "A Simple Preparation of Adamantane". J. Am. Chem. Soc. 79: 3292–3292. doi:10.1021/ja01569a086.  
  8. ^ Schleyer, P. von R.; Donaldson, M. M.; Nicholas, R. D.; Cupas, C. (1973), "Adamantane", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p0016  ; Coll. Vol. 5: 16  
  9. ^ V Vijayakumar et al (2001). "Pressure induced phase transitions and equation of state of adamantane". J. Phys.: Condens. Matter 13: 1961–1972. doi:10.1088/0953-8984/13/9/318.  
  10. ^ Watanabe, Keiji; et al. (2001). "Resist Composition and Pattern Forming Process". United States Patent Application 20010006752. Bandwidth Market, Ltd. http://www.bandwidthmarket.com/resources/patents/apps/. Retrieved 14 October 2005.  
  11. ^ Morcombe, Corey R.; Zilm, Kurt W. (2003). "Chemical Shift referencing in MAS solid state NMR". J. Magn. Reson. 162 (2): 479–486. doi:10.1016/S1090-7807(03)00082-X. PMID 12810033.  
  12. ^ Lenzke, K. ; Landt, L.; Hoener, M. 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.  
  13. ^ Vitall, J. J. (1996). "The Chemistry of Inorganic and Organometallic Compounds with Adamantane-Like Structures". Polyhedron 15: 1585–1642. doi:10.1016/0277-5387(95)00340-1.  







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