Adamantane

Jump to: navigation, search
Template:Chembox E numberTemplate:Chembox SolubilityInWater
Adamantane
IUPAC name Tricyclo[3.3.1.13,7]decane
Identifiers
3D model (JSmol)
ECHA InfoCard Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
Properties
C10H16
Molar mass 136.23 g/mol
Appearance White to off-white powder
Density 1.07 g/cm³ (20 °C), solid
Melting point
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
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

WikiDoc Resources for Adamantane

Articles

Most recent articles on Adamantane

Most cited articles on Adamantane

Review articles on Adamantane

Articles on Adamantane in N Eng J Med, Lancet, BMJ

Media

Powerpoint slides on Adamantane

Images of Adamantane

Photos of Adamantane

Podcasts & MP3s on Adamantane

Videos on Adamantane

Evidence Based Medicine

Cochrane Collaboration on Adamantane

Bandolier on Adamantane

TRIP on Adamantane

Clinical Trials

Ongoing Trials on Adamantane at Clinical Trials.gov

Trial results on Adamantane

Clinical Trials on Adamantane at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on Adamantane

NICE Guidance on Adamantane

NHS PRODIGY Guidance

FDA on Adamantane

CDC on Adamantane

Books

Books on Adamantane

News

Adamantane in the news

Be alerted to news on Adamantane

News trends on Adamantane

Commentary

Blogs on Adamantane

Definitions

Definitions of Adamantane

Patient Resources / Community

Patient resources on Adamantane

Discussion groups on Adamantane

Patient Handouts on Adamantane

Directions to Hospitals Treating Adamantane

Risk calculators and risk factors for Adamantane

Healthcare Provider Resources

Symptoms of Adamantane

Causes & Risk Factors for Adamantane

Diagnostic studies for Adamantane

Treatment of Adamantane

Continuing Medical Education (CME)

CME Programs on Adamantane

International

Adamantane en Espanol

Adamantane en Francais

Business

Adamantane in the Marketplace

Patents on Adamantane

Experimental / Informatics

List of terms related to Adamantane

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]


Overview

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.

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.[10]

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.[11]

References

  1. "SID 152429 -- PubChem Substance Summary". Unknown parameter |accessyear= ignored (|access-date= suggested) (help); Unknown parameter |accessmonthday= ignored (help)
  2. "ADAMANTANE(TRICYCLO(3.3.1.1)DECANE)". Unknown parameter |accessyear= ignored (|access-date= suggested) (help); Unknown parameter |accessmonthday= ignored (help)
  3. Landa, S.; Machácek, V. (1933). Collection Czech. Chem. Commun. 5: 1. Missing or empty |title= (help)
  4. Alexander Senning. Elsevier's Dictionary of Chemoetymology. Elsevier, 2006. ISBN 0444522395.
  5. Prelog, V., Seiwerth,R. (1941). Berichte. 74: 1644 and 1769. Missing or empty |title= (help)
  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. Unknown parameter |accessyear= ignored (|access-date= suggested) (help); Unknown parameter |accessmonthday= ignored (help)
  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. Text "Morcombe, C. R. and Zilm, K. W. " ignored (help)
  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.
  11. Vitall, J. J., "The Chemistry of Inorganic and Organometallic Compounds with Adamantane-Like Structures", Polyhedron, 1996, 15, 1585-1642


Influenza Microchapters

Home

Patient Information

Overview

Historical Perspective

Classification

Pathophysiology

Causes

Differentiating Influenza from other Diseases

Epidemiology and Demographics

Risk Factors

Natural History, Complications and Prognosis

Diagnosis

History and Symptoms

Physical Examination

Laboratory Findings

Chest X Ray

Other Diagnostic Studies

Treatment

Medical Therapy

Primary Prevention

Cost-Effectiveness of Therapy

Future or Investigational Therapies

Case Studies

Case #1

Adamantane On the Web

Most recent articles

Most cited articles

Review articles

CME Programs

Powerpoint slides

Images

American Roentgen Ray Society Images of Adamantane

All Images
X-rays
Echo & Ultrasound
CT Images
MRI

Ongoing Trials at Clinical Trials.gov

US National Guidelines Clearinghouse

NICE Guidance

FDA on Adamantane

CDC on Adamantane

Adamantane in the news

Blogs on Adamantane

Directions to Hospitals Treating Influenza

Risk calculators and risk factors for Adamantane


de:Adamantan nl:Adamantaan sk:Adamantán



Linked-in.jpg