# Cuneane

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> Source: https://en.wikipedia.org/wiki/Cuneane
> Source revision: 1316875189
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{{Short description|Saturated hydrocarbon compound (C8H8)}}
{{Chembox
| ImageFile = Cuneane-HF-Mercury-3D-balls.png
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 160
| ImageName = Ball and stick model of cuneane (1R,2R,3S,4S,5S,6R,7R,8S)
| PIN = Pentacyclo[3.3.0.0<sup>2,4</sup>.0<sup>3,7</sup>.0<sup>6,8</sup>]octane
|Section1={{Chembox Identifiers
| CASNo = 20656-23-9
| CASNo_Ref = {{cascite|correct|??}}
| PubChem = 140734
| ChemSpiderID = 124127
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| SMILES = C12C3C4C3C5C1C2C45
| StdInChI = 1S/C8H8/c1-2-5(1)6-3-4(6)8(2)7(1)3/h1-8H
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YIJMEXRVJPVGIY-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| C=8 | H=8 
| Density = 1.578 g/ml
}}
}}

'''Cuneane''' ({{ety|la|[cuneus](/source/%3Awikt%3Acuneus)|wedge}}<ref>{{cite journal
 |author1=R. Criegee |author2=R. Askani | title = Octamethylsemibullvalene 
 | journal = [Angewandte Chemie International Edition in English](/source/Angewandte_Chemie_International_Edition_in_English) 
 | volume = 7
 | issue = 7
 | year = 1968
 | pages = 537
 | doi = 10.1002/anie.196805371}}</ref>) is a [saturated](/source/Saturated_and_unsaturated_compounds) [hydrocarbon](/source/hydrocarbon) with the [formula](/source/Chemical_formula) {{chem2|C8H8}} and a [3D structure](/source/Molecular_geometry) resembling a [wedge](/source/wedge), hence the name. Cuneane may be produced from [cubane](/source/cubane) by [metal-ion-catalyzed σ-bond rearrangement](/source/metal-ion-catalyzed_%CF%83-bond_rearrangement).<ref>{{cite book
 |author1=Michael B. Smith |author2=Jerry March | title =March's Advanced Organic Chemistry
 | edition = 5th
 | publisher = John Wiley & Sons, Inc.
 | year = 2001
 | pages = 1459
 | isbn = 0-471-58589-0}}</ref><ref>{{cite journal
 |author1=Philip E. Eaton |author2=Luigi Cassar |author3=Jack Halpern | title = Silver(I)- and palladium(II)-catalyzed isomerizations of cubane. Synthesis and characterization of cuneane
 | journal = [Journal of the American Chemical Society](/source/Journal_of_the_American_Chemical_Society)
 | volume = 92
 | issue = 21
 | year =  1970
 | pages = 6366–6368
 | doi = 10.1021/ja00724a061
 |bibcode=1970JAChS..92.6366E }}</ref> Similar reactions are known for {{chem name|homocubane}} ({{chem2|C9H10}}) and bishomocubane ({{chem2|C10H12}}).<ref>{{cite journal
 |author1=Leo A. Paquette |author2=John C. Stowell | title = Silver ion catalyzed rearrangements of strained sigma. bonds. Application to the homocubyl and 1,1'-bishomocubyl systems
 | journal = [Journal of the American Chemical Society](/source/Journal_of_the_American_Chemical_Society)
 | volume = 92
 | issue = 8
 | year =  1970
 | pages = 2584–2586
 | doi = 10.1021/ja00711a082
 |bibcode=1970JAChS..92.2584P }}</ref><ref>{{cite journal
 |author1=W. G. Dauben |author2=M. G. Buzzolini |author3=C. H. Schallhorn |author4=D. L. Whalen |author5=K. J. Palmer | title = Thermal and silver ion catalyzed isomerization of the 1,1′-bishomocubane system: preparation of a new C10H10 isomer 
 | journal = [Tetrahedron Letters](/source/Tetrahedron_Letters)
 | volume = 11
 | issue = 10
 | year =  1970
 | pages = 787–790  
 | doi = 10.1016/S0040-4039(01)97830-X
 }}</ref> <!--<ref>{{cite journal
 |author1=K. Kindler |author2=K. Lührs | title = Studien über den Mechanismus chemischer Reaktionen, XXIII. Hydrierungen von Nitrilen unter Verwendung von Terpenen als Wasserstoffdonatoren 
 | journal = [Chemische Berichte](/source/Chemische_Berichte)
 | volume = 99
 | year =  1966
 | pages = 227–232
 | doi =10.1002/cber.19660990135
 }}</ref> -->

:thumb|left|300px|Synthesis of cuneane from cubane{{clear-left}}

== Molecular geometry ==
The carbon atoms in the cuneane molecule form a [hexahedron](/source/hexahedron) with [point group C<sub>2v</sub>](/source/Molecular_symmetry).
The cuneane molecule has three kinds of equivalent carbon atoms (A, B, C), which have also been confirmed by [NMR](/source/NMR).<ref>{{cite journal|author1=H. Guenther|author2=W. Herrig|doi=10.1002/cber.19731061217|issue=12|journal=[Chemische Berichte](/source/Chemische_Berichte)|pages=3938–3950|title=Anwendungen der <sup>13</sup>C-Resonanz-Spektroskopie, X. <sup>13</sup>C,<sup>13</sup>C-Kopplungskonstanten in Methylencycloalkanen|volume=106|year=1973}}</ref> The molecular graph of the carbon skeleton of cuneane is a [regular graph](/source/regular_graph) with non-equivalent groups of vertices, and so it is a very important test object for different algorithms of [mathematical chemistry](/source/mathematical_chemistry).<ref>{{cite journal
 |author1=M.I. Trofimov |author2=E.A. Smolenskii | title = Electronegativity of atoms of ring-containing molecules—NMR spectroscopy data correlations: a description within the framework of the topological index approach 
 | journal = Russian Chemical Bulletin
 | year =  2000
 | volume = 49
 | issue = 3
 | pages =  402
 | doi = 10.1007/BF02494766|s2cid=95809728 }}</ref><ref>{{cite journal
 |author1=M.I. Trofimov |author2=E.A. Smolenskii | title = Application of the electronegativity indices of organic molecules to tasks of chemical informatics 
 | journal = Russian Chemical Bulletin
 | year =  2005
 | volume = 54
 | issue = 9
 | pages =  2235
 | doi = 10.1007/s11172-006-0105-6|s2cid=98716956 }}</ref> 
 
:thumb|left|120px|Equivalent carbon atoms in cuneane{{clear-left}}

== Derivatives ==
Some cuneane derivatives have [liquid crystal](/source/liquid_crystal) properties.<ref>{{cite journal
 |author1=Bényei, Gyula |author2=Jalsovszky, István |author3=Demus, Dietrich |author4=Prasad, Krishna |author5=Rao, Shankar |author6=Vajda, Anikó |author7=Jákli, Antal |author8=Fodor-Csorba, Katalin | title = First liquid crystalline cuneane-caged derivatives: a structure-property relationship study   
 | journal = Liquid Crystals  
 | year = 2006  
 | volume = 33 
 | issue = 6 
 | pages = 689–696  
 | doi = 10.1080/02678290600722940|bibcode=2006LoCr...33..689B |s2cid=97269476 }}</ref>

==References==
{{Reflist}}

Category:Polycyclic nonaromatic hydrocarbons
Category:Cyclopropanes
Category:Cyclobutanes

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Adapted from the Wikipedia article [Cuneane](https://en.wikipedia.org/wiki/Cuneane) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Cuneane?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.