The Creation Wiki is made available by the NW Creation Network
Watch monthly live webcast - Like us on Facebook - Subscribe on YouTube

Adamantane

From CreationWiki, the encyclopedia of creation science
Jump to: navigation, search
Adamantane
Adamantane skeleton.pngAdamantane Crystals.jpg
General
Systematic name Tricyclo[3.3.1.13,7]decane[1]
Molecular formula C10H16
Molar mass 136.238 g/mol[2]
Appearance white to off-white powder
CAS number 281-23-2[1]
Properties
Density and phase 1.07 g/cm3
Solubility in water insoluble in water[3]
Solubility in other solvents Soluble in hydrocarbons[1]
Melting point 270°C[3]
Boiling point sublimes[1]
Structure
Coordination
geometry
4
Crystal structure cubic, space group Fm3m
Dipole moment 0 D[1]
Hazards
Main hazards Flammable[1]
Related compounds
Related compounds Memantine, NH2

Rimantadine, H2N

Amantadine, NH2[1]

Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Disclaimer and references

Adamantane is a diamondoid that was synthesized in 1941. Diamondoids are carbon cage molecules, which are the smallest unit cage structure of the diamond crystal lattice. It is a hydrocargon composed of ten carbon atoms and sixteen hydrogen atoms. Its derivatives are used in drugs, especially antivirals for ailments such as influenza and Parkinson's disease. It can also be potentially harmful to the body if it comes into contact with the skin, eyes, or is consumed.

Properties

Chemical

Adamantane is an organic substance that can be toxic to aquatic life and can have harmful or irritating effects on humans if excessive exposure occurs.[3] This substance and all of its derivatives are very highly reactive.[1] It is known to be able to block ion channels, preventing the multiplication of various viruses. This is why adamantane's derivatives are so useful in the medical field.[4]

Physical

Adamantane has a cage-like structure composed of Hydrogen (white) and Carbon (black).

Adamantane is a colorless, diamond-shaped solid[5] that has good thermal stability and can be distilled via water vapor distillation process. It smells similar to camphor (C₁₀H₁₆O) and has a higher melting point than all other Hydrocarbons with similar molecular weights. It is the most simple diamondoid and is also a cycloalkane.[3]

The actual adamantane molecule has three Cyclohexane rings (each ring is cycloalkane with a formula of C6H12) and is oriented in the "armchair" formation. The distance between the Hydrogen and Carbon in the molecule is about 1.112Å (Angstrom, which is 1/10,000,000,000 meters) and the length between the Carbons bonded is around 1.54Å-- this is almost the same as bonds in a diamond.[3]

While adamantane is not soluble in water, it is soluble in a few organic liquids, including hydrocarbons.[3]

Synthesis / Occurrences

H. Decker suggested the existence of a Hydrocarbon with the strength of a diamond.

At a conference in the year 1924, H. Decker put forth the idea that there may be a Hydrocarbon with a molecular structure comparable to a diamond. This hypothetical molecule, dubbed "Decaterpene", would have the formula C10H16.[3]

There was a lot of effort put in to try to synthesize this compound. Hans Meerwein used Piperidine to react Diethyl and Formaldehyde, but instead of the fabled "Decaterpene" got 1, 3, 5, 7-tetracarbomethoxybicyclo [3.3.1] nonane-2, 6-dione, which was named "Meerwein's Ester". It should be noted that Meerwein's Ester was actually used in the process of synthesizing not only adamantane, but all of its derivatives as well.[3]

In 1932, adamantine was discovered amid crude oil via fractional distillation[5] by V. Machacek and S. Landa.[3] This relied on the constituents of the oil having differing boiling points.[5] They heated the petroleum to the point where all impurities left behind were completely solid, and then the steam went through a fractional distillation column. The hydrocarbon fractions ended up condensing in the column at different points (according to each respective boiling point) due to the temperature decrease of the column. Very little of the substance was actually produced during this process, but everyone took note of the high boiling and melting point.[3] However, it wasn't given much attention until the substance was synthesized[5] by Vladimir Prelog in 1941.[6] Prelog used a very complicated method in synthesizing adamantane from Meerwein's Ester[3] from larger organic molecules[5]. Thankfully, Paul von Ragué Schleyer accidentally discovered a much simpler process in 1959[3], a two-stage hydrogenation and restructuring process using dicyclopentadiene, a naptha derivative.[5]

Derivatives of adamantane include:

  • 2-Adamantanone or C10H14O
  • 1-Acetamidoadamantane or C12H19NO
  • 1,3-Dihydroxyadamantane (1,3-Adamantanediol) C10H16O2
  • 2-Aminoadamantane Hydrochloride or C10H17NHC
  • 1-Chloro-3,5- Dimethyladamantane or C12H19Cl
  • 1-Adamantanemethanol (1-Adamantylmethanol) C11H18O
  • 1-Adamantyl methyl ketone (1-Acetyladamantane) or C12H18O
  • 2-Adamantanol (2-Hydroxyadamantane) or C10H16O
  • 1-Aminoadamantane Sulfate ( Bis[1-Aminotricyclo (3.3.1.1.3.7)decane]sulfate) or (C10H17N)2H2SO4
  • 1- Amino -3-Hydroxy –Adamantane or C10H17NO

Uses

Adamantane is used in multiple antiviral drugs and vaccines.

One of the main uses for adamantane is in the medical realm. However, it should be noted that, in it's pure form, adamantane is never used medically. Only certain derivatives of this compound are used as antiviral medicines, including the treatment of Parkinson's disease[3] and the Influenza A virus, as well as HIV, herpes, and hepatitis,[5] however Swine Flu and H1N1 can resist adamantane-based antivirals. Derivative drugs include karmantadin, tromantadine, dopamantin, memantine, vildagliptin, and rinmantadine.[3]

When it comes to influenza A, there is a membrane called M2, and it functions as an ion channel during some of the stages of replication inside the host cell of the virus. This is at the fusion of viral membrane and endosome membrane stages, which is when new virions are made and released. Thankfully, adamantine antivirals effectively block the ion channel, preventing any replication of the virus.[4]

Other uses for adamantine include dry-etching masks, extending life of Gain Medium in Dye Lasers, making polymer formulations, and in solid-state NMR spectroscopy.[3]

Possible Heath Issues

If adamantane comes into contact with the eyes, it can cause irritation.

Like most other substances, adamantane can be harmful or irritating if exposed to certain areas or too much substance is used.[3]

For humans, adamantane can irritate both the skin and eyes. In the case of exposure to the eyes, the compound should be washed out with a generous amount of water right away before going to a hospital for further treatment. Skin irritation isn't as serious, but should still be washed with soap and water immediately and the clothes that are affected should be washed before re-wearing. Now, if a person ingests adamantane, they are going to need to immediately get medical help. It is suggested that they drink 2-4 glasses of either milk or water so that the compound is diluted, but vomiting should not be forced or induced. And if the compound causes respiratory problems, then the person needs to get immediate medical assistance to receive oxygen or even artificial respiratory help. [3]

This compound should be disposed of properly as it can cause serious damage the environment, specifically aquatic life. [2]

Video

A video displaying the structure of adamantine.

References

  1. 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 Adamantane Wikipedia. Web. Last modified 6 January, 2018. Authors unknown.
  2. 2.0 2.1 Adamantane Pubchem. Web. Accessed 18 February, 2018. Author unknown.
  3. 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 3.10 3.11 3.12 3.13 3.14 3.15 3.16 Adamantane Chemistry Learner. Web. Accessed 18 February, 2018. Author unknown.
  4. 4.0 4.1 Adamantane antivirals Drugs.com. Web. Accessed March 17, 2018. Author Unknown.
  5. 5.0 5.1 5.2 5.3 5.4 5.5 5.6 Clegg, Brian. Adamantane Chemistry World. Web. Published 26 January, 2017.
  6. Molecule of the Week Archive Adamantane American Chemical Society. Web. Last Updated October 5, 2017. Author Unknown.