Iceane

Iceane
Names
	IUPAC name Tetracyclo[5.3.1.12,6.04,9]dodecane
	Other names Wurtzitane
Identifiers
CAS Number	53283-19-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	26333278 ;
PubChem CID	595503;
CompTox Dashboard (EPA)	DTXSID70344261 ;
	InChI InChI=1S/C12H18/c1-7-2-11-3-8(1)10-4-9(7)5-12(11)6-10/h7-12H,1-6H2/t7-,8+,9+,10-,11-,12+ Key: KZNNISMAUNEBPT-KUDAMMAASA-N ; InChI=1/C12H18/c1-7-2-11-3-8(1)10-4-9(7)5-12(11)6-10/h7-12H,1-6H2/t7-,8+,9+,10-,11-,12+ Key: KZNNISMAUNEBPT-KUDAMMAABM;
	SMILES C1C2CC3CC1C4CC2CC3C4;
Properties
Chemical formula	C12H18
Molar mass	162.276 g·mol−1
Melting point	325 °C (617 °F; 598 K)
Boiling point	Sublimes
Structure
Point group	D3h
Dipole moment	0 D
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Iceane is a saturated polycyclic hydrocarbon with formula C₁₂H₁₈. It has a cage-like molecular structure, whose carbon skeleton can be viewed as three fused cyclohexane rings in the boat conformation; or as two such rings in the chair conformation, connected by three parallel axial bonds. The spatial arrangement of carbon atoms in iceane is the lonsdalite crystalline structure.

The name "iceane" was proposed by the chemist Louis Fieser about a decade before the compound was first prepared. He was carrying out studies on the arrangement of water molecules in ice, when it occurred to him that there could exist a stable hydrocarbon with the above structure.^[3]^[4]

It is also referred to as wurtzitane,^[5] due to its similarity to the wurtzite crystal structure;^[1] however, the name "iceane" has precedence.

References

^ ^a ^b ^c Hamon, D. P. G.; Taylor, G. F. (1976). "A synthesis of tetracyclo[5,3,1,1^2,6,0^4,9]dodecane (iceane)". Aust. J. Chem. 29 (8): 1721–1734. doi:10.1071/CH9761721.
^ Cupas, Chris A.; Hodakowski, Leonard (July 1974). "Iceane". Journal of the American Chemical Society. 96 (14): 4668–4669. doi:10.1021/ja00821a050.
^ Fieser, L. F. (1965). "Extensions in the use of plastic tetrahedral models". J. Chem. Educ. 42 (8): 408–412. doi:10.1021/ed042p408.
^ Hargittai, M.; Hargittai, I. (2013). "Polyhedral Molecular Geometries". In Senechal, M. (ed.). Shaping Space: Exploring Polyhedra in Nature, Art, and the Geometrical Imagination. Springer Science & Business Media. pp. 153–170, 299. ISBN 9780387927145.
^ Tobler, H.; Klaus, R. O.; Ganter, C. (1975). "Wurtzitan (Tetracyclo[5.3.1.1^2,6.0^4,9]dodecan)". Helv. Chim. Acta. 58 (5): 1455–1464. doi:10.1002/hlca.19750580522.

External links

[Hamon1976-1] Hamon, D. P. G.; Taylor, G. F. (1976). "A synthesis of tetracyclo[5,3,1,1^2,6,0^4,9]dodecane (iceane)". Aust. J. Chem. 29 (8): 1721–1734. doi:10.1071/CH9761721.

[Cupas1974-2] Cupas, Chris A.; Hodakowski, Leonard (July 1974). "Iceane". Journal of the American Chemical Society. 96 (14): 4668–4669. doi:10.1021/ja00821a050.

[3] Fieser, L. F. (1965). "Extensions in the use of plastic tetrahedral models". J. Chem. Educ. 42 (8): 408–412. doi:10.1021/ed042p408.

[4] Hargittai, M.; Hargittai, I. (2013). "Polyhedral Molecular Geometries". In Senechal, M. (ed.). Shaping Space: Exploring Polyhedra in Nature, Art, and the Geometrical Imagination. Springer Science & Business Media. pp. 153–170, 299. ISBN 9780387927145.

[5] Tobler, H.; Klaus, R. O.; Ganter, C. (1975). "Wurtzitan (Tetracyclo[5.3.1.1^2,6.0^4,9]dodecan)". Helv. Chim. Acta. 58 (5): 1455–1464. doi:10.1002/hlca.19750580522.

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See also

References

External links