Chemistry:Iceane

Iceane

Names
IUPAC name Tetracyclo[5.3.1.12,6.04,9]dodecane
Other names Wurtzitane
Identifiers
CAS Number	53283-19-5 Y
3D model (JSmol)	Interactive image
ChemSpider	26333278 Y
PubChem CID	595503
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	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).
N verify (what is YN ?)
Infobox references

Iceane is a saturated polycyclic hydrocarbon with formula C
12H
18. 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.

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

See also

• Adamantane
• Twistane
• Propellane
• Hexanitrohexaazaisowurtzitane

External links

• Royal Society of Chemistry Journal
• Symmetry Through the Eyes of a Chemist, Magdolna Hargittai
• A Basis for Synthesis Design, Tse-Lok Ho
• Structures and Energies of Polycyclic Hydrocarbons, Joan E. Shields