This MedLibrary.org supplementary page on Cyclobutane is provided directly from the open source Wikipedia as a service to our readers. Please see the note below on authorship of this content, as well as the Wikipedia usage guidelines. To search for other content from our encyclopedia supplement, please use the form below:
Related Sponsors
| Cyclobutane | |
|---|---|
 |
|
 |
 |
| IUPAC name | cyclobutane |
| Identifiers | |
| CAS number | 00287-23-0 |
| SMILES |
|
| 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 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.
Cyclobutanes are cyclobutane derivatives.
Contents |
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 conformation 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 acid3 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. 4 Some related fenestranes are also found in nature.citation needed
References
- ^ chemical compound :: Cycloalkanes - Britannica Online Encyclopedia
- ^ http://www.westminster.edu/staff/Kailbw/CH2b.pdf
- ^ J. S. Sinninghe Damsté, M. Strous, W. I. C. Rijpstra, E. C. Hopmans, J. A. J. Geenevasen, A. C. T. van Duin, L. A. van Niftrik and M. S. M. Jetten (2002). "Linearly concatenated cyclobutane lipids form a dense bacterial membrane". Nature 419: 708–712. doi:.
- ^ Vincent Mascitti and E. J. Corey (2006). "Enantioselective Synthesis of Pentacycloanammoxic Acid". J. Am. Chem. Soc. 128 (10): 3118. doi:.Authors state that mode of biosynthesis is quite mysterious
External links
- Datasheet Link
- Molview from bluerhinos.co.uk See Cyclobutane in 3D
|
|||||
Wikipedia content modification information:
- This page was last modified on 18 October 2008, at 09:02.
Wikipedia Authorship and Review
Wikipedia content provided here is not reviewed directly by MedLibrary.org. Wikipedia content is authored by an open community of volunteers and is not produced by or in any way affiliated with MedLibrary.org.
Wikipedia Usage Guidelines
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article on "Cyclobutane".
The URL for this specific entry is:
All Wikipedia text is available under the terms of the GNU Free Documentation License. (See Copyrights for details). Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc.