Cuneane

Cuneane
Identifiers
CAS Number	20656-23-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	124127 ;
PubChem CID	140734;
CompTox Dashboard (EPA)	DTXSID20942857 ;
	InChI InChI=1S/C8H8/c1-2-5(1)6-3-4(6)8(2)7(1)3/h1-8H Key: YIJMEXRVJPVGIY-UHFFFAOYSA-N ;
	SMILES C12C3C4C3C5C1C2C45;
Properties
Chemical formula	C8H8
Molar mass	104.152 g·mol−1
Density	1.578 g/ml
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Cuneane (C₈H₈, pentacyclo[3.3.0.0^2,4.0^3,7.0^6,8]octane) is a saturated hydrocarbon.[1] Its name is derived from the Latin cuneus, meaning a wedge.[2] Cuneane may be produced from cubane by metal-ion-catalyzed σ-bond rearrangement.[3][4] Similar reactions are known for homocubane (C₉H₁₀) and bishomocubane (C₁₀H₁₂).[5][6]

Scheme 1. Synthesis of cuneane from cubane

Molecular geometry

The carbon atoms in the cuneane molecule form a hexahedron with point group C_2v. The cuneane molecule has three groups of equivalent carbon atoms (A, B, C), which have also been confirmed by NMR.[7] The molecular graph of the carbon skeleton of cuneane is a regular graph with non-equivalent groups of vertices, and so it is a very important test object for different algorithms of mathematical chemistry.[8][9]

Derivatives

Some cuneane derivatives have liquid crystal properties.[10]

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References

with 3D-structure (however molecular graph of cuneane is a planar graph)
R. Criegee; R. Askani (1968). "Octamethylsemibullvalene". Angewandte Chemie International Edition in English. 7 (7): 537. doi:10.1002/anie.196805371.
Michael B. Smith; Jerry March (2001). March’s Advanced Organic Chemistry (5th ed.). John Wiley & Sons, Inc. p. 1459. ISBN 0-471-58589-0.
Philip E. Eaton; Luigi Cassar; Jack Halpern (1970). "Silver(I)- and palladium(II)-catalyzed isomerizations of cubane. Synthesis and characterization of cuneane". Journal of the American Chemical Society. 92 (21): 6366–6368. doi:10.1021/ja00724a061.
Leo A. Paquette; John C. Stowell (1970). "Silver ion catalyzed rearrangements of strained sigma. bonds. Application to the homocubyl and 1,1'-bishomocubyl systems". Journal of the American Chemical Society. 92 (8): 2584–2586. doi:10.1021/ja00711a082.
W. G. Dauben; M. G. Buzzolini; C. H. Schallhorn; D. L. Whalen; K. J. Palmer (1970). "Thermal and silver ion catalyzed isomerization of the 1,1′-bishomocubane system: preparation of a new C₁₀H₁₀isomer". Tetrahedron Letters. 11 (10): 787–790. doi:10.1016/S0040-4039(01)97830-X.
H. Guenther; W. Herrig (1973). "Anwendungen der ¹³C-Resonanz-Spektroskopie, X. ¹³C,¹³C-Kopplungskonstanten in Methylencycloalkanen". Chemische Berichte. 106 (12): 3938–3950. doi:10.1002/cber.19731061217.
M.I. Trofimov; E.A. Smolenskii (2000). "Electronegativity of atoms of ring-containing molecules—NMR spectroscopy data correlations: a description within the framework of topological index approach". Russian Chemical Bulletin. 49 (3): 402. doi:10.1007/BF02494766.
M.I. Trofimov; E.A. Smolenskii (2005). "Application of the electronegativity indices of organic molecules to tasks of chemical informatics". Russian Chemical Bulletin. 54 (9): 2235. doi:10.1007/s11172-006-0105-6.
Bényei, Gyula; Jalsovszky, István; Demus, Dietrich; Prasad, Krishna; Rao, Shankar; Vajda, Anikó; Jákli, Antal; Fodor‐Csorba, Katalin (2006). "First liquid crystalline cuneane‐caged derivatives: a structure-property relationship study". Liquid Crystals. 33 (6): 689–696. doi:10.1080/02678290600722940.

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[1] with 3D-structure (however molecular graph of cuneane is a planar graph)

[2] R. Criegee; R. Askani (1968). "Octamethylsemibullvalene". Angewandte Chemie International Edition in English. 7 (7): 537. doi:10.1002/anie.196805371.

[3] Michael B. Smith; Jerry March (2001). March’s Advanced Organic Chemistry (5th ed.). John Wiley & Sons, Inc. p. 1459. ISBN 0-471-58589-0.

[4] Philip E. Eaton; Luigi Cassar; Jack Halpern (1970). "Silver(I)- and palladium(II)-catalyzed isomerizations of cubane. Synthesis and characterization of cuneane". Journal of the American Chemical Society. 92 (21): 6366–6368. doi:10.1021/ja00724a061.

[5] Leo A. Paquette; John C. Stowell (1970). "Silver ion catalyzed rearrangements of strained sigma. bonds. Application to the homocubyl and 1,1'-bishomocubyl systems". Journal of the American Chemical Society. 92 (8): 2584–2586. doi:10.1021/ja00711a082.

[6] W. G. Dauben; M. G. Buzzolini; C. H. Schallhorn; D. L. Whalen; K. J. Palmer (1970). "Thermal and silver ion catalyzed isomerization of the 1,1′-bishomocubane system: preparation of a new C₁₀H₁₀isomer". Tetrahedron Letters. 11 (10): 787–790. doi:10.1016/S0040-4039(01)97830-X.

[7] H. Guenther; W. Herrig (1973). "Anwendungen der ¹³C-Resonanz-Spektroskopie, X. ¹³C,¹³C-Kopplungskonstanten in Methylencycloalkanen". Chemische Berichte. 106 (12): 3938–3950. doi:10.1002/cber.19731061217.

[8] M.I. Trofimov; E.A. Smolenskii (2000). "Electronegativity of atoms of ring-containing molecules—NMR spectroscopy data correlations: a description within the framework of topological index approach". Russian Chemical Bulletin. 49 (3): 402. doi:10.1007/BF02494766.

[9] M.I. Trofimov; E.A. Smolenskii (2005). "Application of the electronegativity indices of organic molecules to tasks of chemical informatics". Russian Chemical Bulletin. 54 (9): 2235. doi:10.1007/s11172-006-0105-6.

[10] Bényei, Gyula; Jalsovszky, István; Demus, Dietrich; Prasad, Krishna; Rao, Shankar; Vajda, Anikó; Jákli, Antal; Fodor‐Csorba, Katalin (2006). "First liquid crystalline cuneane‐caged derivatives: a structure-property relationship study". Liquid Crystals. 33 (6): 689–696. doi:10.1080/02678290600722940.