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Encyclopedia > 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) Image File history File links No higher resolution available. ... Image File history File links Size of this preview: 602 × 600 pixelsFull resolution (1100 × 1096 pixel, file size: 152 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ... Image File history File links Size of this preview: 601 × 599 pixelsFull resolution (1100 × 1097 pixel, file size: 251 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...

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: Memantine
Rimantadine
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 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] Adamantane is the most stable isomer of C10H16. Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Enargite crystals In mineralogy and crystallography, a crystal structure is a unique arrangement of atoms in a crystal. ... The cubic crystal system is a crystal system where the unit cell is in the shape of a cube. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... The examples and perspective in this article or section may not represent a worldwide view. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... Memantine is the first in a novel class of Alzheimers disease medications acting on the glutamatergic system. ... Rimantadine (systematic name 1-(1-aminoethyl)adamantane) is an orally administered medicine used to treat, and in rare cases prevent, Influenzavirus A infection. ... Amantadine, 1-aminoadamantane, is an antiviral drug that was approved by the FDA in 1976 for the treatment of influenza type A in adults. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... R-phrases 11-20/21/22-36/37/38 S-phrases 16-26-36 RTECS number EX1260000 (R) EX1250000 (S) Supplementary data page Structure and properties n, εr, etc. ... cyclobutane Cycloalkanes (also called naphthenes) are chemical compounds with one or more carbon rings to which hydrogen atoms are attached according to the formula CnH2n. ... Diamondoid, in the context of building materials for nanotechnology components, most generally refers to structures that resemble diamond in a broad sense: namely, strong, stiff structures containing dense, 3-D networks of covalent bonds, formed chiefly from first and second row atoms with a valence of three or more. ... Pumpjack pumping an oil well near Lubbock, Texas Ignacy Łukasiewicz - inventor of the refining of kerosene from crude oil. ...

Contents

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] Vladimir Prelog (July 23, 1906 – January 7, 1998) was a renowned Bosnian - Croatian chemist who worked in Prague, Zagreb and Zurich and who won the Nobel Prize in chemistry in 1975. ... Paul von Rague Schleyer Paul von Rague Schleyer is one of the most accomplished organic physical chemists of the 20th century. ... Dicyclopentadiene, C10H12, is a hydrocarbon found in oil deposits. ...


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. Dry etching refers to the removal of material, typically a masked pattern of semiconductor material, by exposing the material to a bombardment of ions (usually a plasma of Nitrogen, Chlorine and Boron Trichloride) that dislodge portions of the material from the exposed surface. ... A polymer (from Greek: πολυ, polu, many; and μέρος, meros, part) is a substance composed of molecules with large molecular mass composed of repeating structural units, or monomers, connected by covalent chemical bonds. ...


In solid-state NMR spectroscopy, adamantane is a common standard for chemical shift referencing.[9] Solid-state NMR (SSNMR) spectroscopy is a kind of nuclear magnetic resonance (NMR) spectroscopy, characterized by the presence of anisotropic (directionally dependent) interactions. ... In nuclear magnetic resonance (NMR), the chemical shift describes the dependence of nuclear magnetic energy levels on the electronic environment in a molecule. ...


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.[10] Close-up of a table-top dye laser based on Rhodamine 6G, emitting at 580 nm (yellow-orange). ... Photoionisation is a physical process in which a photon strikes an atom, ion or molecule, resulting in the ejection of an electron. ... Ultraviolet (UV) radiation is electromagnetic radiation of a wavelength shorter than that of the visible region, but longer than that of soft X-rays. ... A diamondoid, in the context of building materials for nanotechnology components, most generally refers to structures that resemble diamond in a broad sense: namely, strong, stiff structures containing dense, 3-D networks of covalent bonds, formed chiefly from first and second row atoms with a valence of three or more. ...


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. Amantadine, 1-aminoadamantane, is an antiviral drug that was approved by the FDA in 1976 for the treatment of influenza type A in adults. ... Memantine is the first in a novel class of Alzheimers disease medications acting on the glutamatergic system. ... Rimantadine (systematic name 1-(1-aminoethyl)adamantane) is an orally administered medicine used to treat, and in rare cases prevent, Influenzavirus A infection. ... Diamondoid, in the context of building materials for nanotechnology components, most generally refers to structures that resemble diamond in a broad sense: namely, strong, stiff structures containing dense, 3-D networks of covalent bonds, formed chiefly from first and second row atoms with a valence of three or more. ... Propellanes are a class of tricyclic organic compounds sharing a common carbon carbon covalent bond. ... Propellanes are a class of tricyclic organic compounds sharing a common carbon carbon covalent bond. ...


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. In organic chemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon. ... Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting primarily of carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well... n-butyllithium, an organometallic compound. ... A persistent carbene (also known as a stable carbene) is a particular carbene demonstrating particular stability despite being a reactive intermediate. ...


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.[11] Phosphorus pentoxide is the chemical compound with the formula P4O10. ... Phosphorus pentasulfide, also called phosphorus sulfide, sulfur phosphide, diphosphorus pentasulfide and phosphorus persulfide, is an inorganic compound of phosphorus and sulfur. ... Hexamine ((CH2)6N4) is a chemical created by the reaction of 6 moles of formaldehyde and 4 moles of ammonia . ...


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. ^ Schleyer, P. von R. (1957). "A Simple Preparation of Adamantane". 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

  Results from FactBites:
 
Reference.com/Encyclopedia/Adamantane (314 words)
Adamantane was first synthesised by Prelog in 1941.
In solid-state NMR spectroscopy, adamantane is a common standard for chemical shift referencing.
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.
Chemical & Engineering News: Latest News - Silicon's Building Block Synthesized (286 words)
Adamantane analog is smallest 3-D repeat unit in the silicon crystal lattice
The compound has the same structure as adamantane, the carbon compound that serves as the repeat unit in diamond, one of carbon’s structural allotropes.
Adamantanes containing several silicon atoms have been prepared before.
  More results at FactBites »

 
 

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