Iceane

Names

IUPAC name

Tetracyclo[5.3.1.1^2,6.0^4,9]dodecane

Other names

Wurtzitane

Identifiers

CAS Number

53283-19-5^Y

3D model (JSmol)

Interactive image

ChemSpider

26333278^Y

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+^N
Key: KZNNISMAUNEBPT-KUDAMMAASA-N^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

163.56 g/mol

Structure

Point group

D_3h

Dipole moment

0 D

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is ^YN ?)

Infobox references

Chemical compound

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.^[1]^[2]

It is also referred to as wurtzitane,^[3] due to its similarity to the wurtzite crystal structure;^[4] however, the name "iceane" has precedence.

References

^ 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.
^ 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.