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Cyclobutane



Cyclobutane
IUPAC name cyclobutane
Identifiers
CAS number 00287-23-0
SMILES C1CCC1
Properties
Molecular formula C4H8
Molar mass 56.107 g/mol
Density 0,720 g/cm3
Melting point

-91 °C

Boiling point

12.5 °C

Related Compounds
Related alkane Butane
Related compounds Cyclobutene; Cyclobutadiene
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Cyclobutane, C4H8, with a molecular mass of 56.107g/mol, is a four carbon alkane in which all the carbon atoms are arranged cyclically, hence cyclobutane. Cyclobutane is a gas and commercially available as a liquefied gas.

Additional recommended knowledge

Cyclobutanes are cyclobutane derivatives.

Conformation

The 90 degree bond angles between carbon atoms are significantly strained and as such have greater bond energies than either linear butane molecules or larger homocyclic alkanes such as cyclohexane. As such, cyclobutane is unstable above about 500 °C.

The chemical conformation of cyclobutane is not planar but folded or "puckered".[1] One of the carbon atoms makes a 25° angle with the plane formed by the other three carbons. In this way some of the hydrogen eclipsing interactions are reduced. The confirmation is also known as a "butterfly".[2] In substituted cycloalkanes both planar and puckered conformations exist. Because the energy difference between the two states can be small they can interconvert.

Cyclobutanes in nature

Despite inherent strain the cyclobutane motif is not an alien to molecules found in nature. One unusual example is pentacycloanammoxic acid which is a ladderane composed of 5 fused cyclobutane units. The estimated strain in this compound is 3 times that of cyclobutane. The compound is found in bacteria performing the anammoxprocess where it forms part of a tight and very dense membrane believed to protect the organism from toxic hydroxylamine and hydrazine involved in the production of nitrogen and water from nitrite ions and ammonia. [3] Some related fenestranes are also found in nature.

References

  1. ^ http://www.britannica.com/eb/article-79615/chemical-compound#615967.hook
  2. ^ http://www.westminster.edu/staff/Kailbw/CH2b.pdf
  3. ^ Enantioselective Synthesis of Pentacycloanammoxic Acid Vincent Mascitti and E. J. Corey J. Am. Chem. Soc.; 2006; 128(10) pp 3118 doi:10.1021/ja058370gAuthors state that mode of biosynthesis is quite mysterious
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Cyclobutane". A list of authors is available in Wikipedia.
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