Cubane

Cubane
Structural formula of cubane
Structural formula of cubane
Ball-and-stick model of cubane
Ball-and-stick model of cubane
Names
Preferred IUPAC name
Cubane[1]
Systematic IUPAC name
Pentacyclo[4.2.0.02,5.03,8.04,7]octane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C8H8/c1-2-5-3(1)7-4(1)6(2)8(5)7/h1-8H checkY
    Key: TXWRERCHRDBNLG-UHFFFAOYSA-N checkY
  • InChI=1/C8H8/c1-2-5-3(1)7-4(1)6(2)8(5)7/h1-8H
    Key: TXWRERCHRDBNLG-UHFFFAOYAL
  • C12C3C4C1C5C2C3C45
Properties
C8H8
Molar mass 104.15 g/mol
Appearance Transparent[2] crystalline solid
Density 1.29 g/cm3
Melting point 133.5 °C (272.3 °F; 406.6 K)[3]
Boiling point 161.6 °C (322.9 °F; 434.8 K)[3]
Related compounds
Related hydrocarbons
 Cuneane
Dodecahedrane
Tetrahedrane
Prismane
Prismane C8
Related compounds
 Octafluorocubane
Octanitrocubane
Octaazacubane
Octasilacubane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cubane is a synthetic hydrocarbon compound with the formula C8H8. It consists of eight carbon atoms arranged at the corners of a cube, with one hydrogen atom attached to each carbon atom. A solid crystalline substance, cubane is one of the Platonic hydrocarbons and a member of the prismanes. It was first synthesized in 1964 by Philip Eaton and Thomas Cole.[4] Before this work, Eaton believed that cubane would be impossible to synthesize due to the "required 90 degree bond angles".[5][6] The cubic shape requires the carbon atoms to adopt an unusually sharp 90° bonding angle, which would be highly strained as compared to the 109.45° angle of a tetrahedral carbon. Once formed, cubane is quite kinetically stable, due to a lack of readily available decomposition paths. It is the simplest hydrocarbon with octahedral symmetry.

Having high potential energy and kinetic stability makes cubane and its derivative compounds useful for controlled energy storage. For example, octanitrocubane and heptanitrocubane have been studied as high-performance explosives. These compounds also typically have a very high density for hydrocarbon molecules. The resulting high energy density means a large amount of energy can be stored in a comparably smaller amount of space, an important consideration for applications in fuel storage and energy transport. Furthermore, their geometry and stability make them suitable isosteres for benzene rings.[7]

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 169. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The retained names adamantane and cubane are used in general nomenclature and as preferred IUPAC names.
  2. ^ "Start".
  3. ^ a b Cite error: The named reference Biegasiewicz was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference eaton-1964 was invoked but never defined (see the help page).
  5. ^ Teachers, University of New South Wales Summer School for Chemistry (1963). Approach to Chemistry: Lectures and Workshop Reports of the ... Summer School for Chemistry Teachers. The University. p. 98. "This compound was described only a few months ago and, curiously enough, it is quite easy to make, although only a year ago I would have predicted that it would be difficult, or even impossible, to synthesize."
  6. ^ Moore, John W.; Stanitski, Conrad L.; Jurs, Peter C. (2002). Chemistry: The Molecular Science. Harcourt College Publishers. p. 372. ISBN 978-0-03-032011-8. "This sharp bond angle creates severe bond strain in cubane, a compound thought previously impossible to synthesize because of the required 90° bond angles."
  7. ^ Wiesenfeldt, Mario P.; Rossi-Ashton, James A.; Perry, Ian B.; Diesel, Johannes; Garry, Olivia L.; Bartels, Florian; Coote, Susannah C.; Ma, Xiaoshen; Yeung, Charles S.; Bennett, David J.; MacMillan, David W. C. (June 2023). "General access to cubanes as benzene bioisosteres". Nature. 618 (7965): 513–518. doi:10.1038/s41586-023-06021-8. ISSN 1476-4687. PMC 10680098.