Cuneane Explained

Cuneane (^[1]) is a saturated hydrocarbon with the formula and a 3D structure resembling a wedge, hence the name. Cuneane may be produced from cubane by metal-ion-catalyzed σ-bond rearrangement.^{[2] [3]} Similar reactions are known for and bishomocubane .^{[4] [5]}

Molecular geometry

The carbon atoms in the cuneane molecule form a hexahedron with point group C_2v.The cuneane molecule has three kinds of equivalent carbon atoms (A, B, C), which have also been confirmed by NMR.^[6] 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.^{[7] [8]}

Derivatives

Some cuneane derivatives have liquid crystal properties.^[9]

Notes and References

1. R. Criegee . R. Askani . Octamethylsemibullvalene . . 7 . 7 . 1968 . 537 . 10.1002/anie.196805371.
2. Book: Michael B. Smith . Jerry March . March's Advanced Organic Chemistry . 5th . John Wiley & Sons, Inc. . 2001 . 1459 . 0-471-58589-0.
3. Philip E. Eaton . Luigi Cassar . Jack Halpern . Silver(I)- and palladium(II)-catalyzed isomerizations of cubane. Synthesis and characterization of cuneane . . 92 . 21 . 1970 . 6366–6368 . 10.1021/ja00724a061 .
4. Leo A. Paquette . John C. Stowell . Silver ion catalyzed rearrangements of strained sigma. bonds. Application to the homocubyl and 1,1'-bishomocubyl systems . . 92 . 8 . 1970 . 2584–2586 . 10.1021/ja00711a082 .
5. W. G. Dauben . M. G. Buzzolini . C. H. Schallhorn . D. L. Whalen . K. J. Palmer . Thermal and silver ion catalyzed isomerization of the 1,1′-bishomocubane system: preparation of a new C10H10 isomer . . 11 . 10 . 1970 . 787–790 . 10.1016/S0040-4039(01)97830-X .
6. H. Guenther. W. Herrig. 10.1002/cber.19731061217. 12. Chemische Berichte. 3938–3950. Anwendungen der ¹³C-Resonanz-Spektroskopie, X. ¹³C,¹³C-Kopplungskonstanten in Methylencycloalkanen. 106. 1973.
7. M.I. Trofimov . E.A. Smolenskii . Electronegativity of atoms of ring-containing molecules—NMR spectroscopy data correlations: a description within the framework of the topological index approach . Russian Chemical Bulletin . 2000 . 49 . 3 . 402 . 10.1007/BF02494766. 95809728 .
8. M.I. Trofimov . E.A. Smolenskii . Application of the electronegativity indices of organic molecules to tasks of chemical informatics . Russian Chemical Bulletin . 2005 . 54 . 9 . 2235 . 10.1007/s11172-006-0105-6. 98716956 .
9. Bényei, Gyula . Jalsovszky, István . Demus, Dietrich . Prasad, Krishna . Rao, Shankar . Vajda, Anikó . Jákli, Antal . Fodor‐Csorba, Katalin . First liquid crystalline cuneane‐caged derivatives: a structure-property relationship study . Liquid Crystals . 2006 . 33 . 6 . 689–696 . 10.1080/02678290600722940. 97269476 .