Editing Cubane (section)

{{Short description|Organic compound (C8H8) with a cube carbon structure}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 443545029
| Name = Cubane
| ImageFileL1 = Cuban.svg
| ImageNameL1 = Structural formula of cubane
| ImageClassL1   = skin-invert
| ImageFileR1 = Cubane molecule ball.png
| ImageNameR1 = Ball-and-stick model of cubane
| PIN = Cubane<ref name=iupac2013>{{cite book | title =  Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 169 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The retained names adamantane and cubane are used in general nomenclature and as preferred IUPAC names.}}</ref>
| SystematicName = Pentacyclo[4.2.0.0<sup>2,5</sup>.0<sup>3,8</sup>.0<sup>4,7</sup>]octane
| OtherNames = 
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 119867
| PubChem = 136090
| InChIKey = TXWRERCHRDBNLG-UHFFFAOYAL
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H8/c1-2-5-3(1)7-4(1)6(2)8(5)7/h1-8H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = TXWRERCHRDBNLG-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 277-10-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Z5HM0Q7DK1
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 33014
| SMILES = C12C3C4C1C5C2C3C45
| InChI = 1/C8H8/c1-2-5-3(1)7-4(1)6(2)8(5)7/h1-8H
  }}
|Section2={{Chembox Properties
| Formula = {{chem2|C8H8}}
| MolarMass = 104.15 g/mol
| Density = 1.29 g/cm<sup>3</sup>
| Appearance = Transparent<ref name=ch>{{cite web | url=https://www.ch.ic.ac.uk/local/projects/b_muir/Cubane/Cubanepro/Start.html | title=Start }}</ref> crystalline solid
| MeltingPtC = 133.5 
| MeltingPt_ref = <ref name = Biegasiewicz />
| BoilingPtC = 161.6
| BoilingPt_ref = <ref name= Biegasiewicz />
  }}
|Section8={{Chembox Related
| OtherFunction = [[Cuneane]]<br />[[Dodecahedrane]]<br />[[Tetrahedrane]]<br />[[Prismane]]<br />[[Prismane C8]]
| OtherFunction_label = [[hydrocarbon]]s
| OtherCompounds = [[Octafluorocubane]]<br />[[Octanitrocubane]]<br />[[Octaazacubane]]<br />[[Mirex]]
  }}
}}
'''Cubane''' is a synthetic [[hydrocarbon]] compound with the [[Chemical formula|formula]] {{chem2|C8H8}}. It consists of eight [[carbon]] atoms arranged at the corners of a [[Cube (geometry)|cube]], with one [[hydrogen]] atom attached to each carbon atom. A solid [[crystal]]line substance, cubane is one of the [[Platonic hydrocarbon]]s and a member of the [[prismanes]]. It was first synthesized in 1964 by [[Philip Eaton]] and Thomas Cole.<ref name="eaton-1964" /> Before this work, Eaton believed that cubane would be impossible to synthesize due to the "required 90 degree [[molecular geometry|bond angles]]".<ref>{{cite book |last1=Teachers |first1=University of New South Wales Summer School for Chemistry |title=Approach to Chemistry: Lectures and Workshop Reports of the ... Summer School for Chemistry Teachers |date=1963 |publisher=The University |page=98 |url=https://books.google.com/books?id=cFA0AQAAIAAJ |language=en}} "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."</ref><ref>{{cite book |last1=Moore |first1=John W. |last2=Stanitski |first2=Conrad L. |last3=Jurs |first3=Peter C. |title=Chemistry: The Molecular Science |date=2002 |publisher=Harcourt College Publishers |isbn=978-0-03-032011-8 |page=372 |url=https://books.google.com/books?id=XjcvAQAAIAAJ |language=en}} "This sharp bond angle creates severe bond strain in cubane, a compound thought previously impossible to synthesize because of the required 90° bond angles."</ref> The cubic shape requires the carbon atoms to adopt an unusually sharp 90° bonding angle, which would be highly [[strain (chemistry)|strained]] as compared to the [[tetrahedral molecular geometry#Tetrahedral bond angle|109.45° angle]] of a [[tetrahedral geometry|tetrahedral]] carbon. Once formed, cubane is quite [[kinetic stability|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 [[isostere]]s for benzene rings.<ref>{{Cite journal |last1=Wiesenfeldt |first1=Mario P. |last2=Rossi-Ashton |first2=James A. |last3=Perry |first3=Ian B. |last4=Diesel |first4=Johannes |last5=Garry |first5=Olivia L. |last6=Bartels |first6=Florian |last7=Coote |first7=Susannah C. |last8=Ma |first8=Xiaoshen |last9=Yeung |first9=Charles S. |last10=Bennett |first10=David J. |last11=MacMillan |first11=David W. C. |date=June 2023 |title=General access to cubanes as benzene bioisosteres |journal=Nature |language=en |volume=618 |issue=7965 |pages=513–518 |doi=10.1038/s41586-023-06021-8 |pmid=37015289 |issn=1476-4687|pmc=10680098 |bibcode=2023Natur.618..513W }}</ref>