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.

Iceane
Iceane-3D-sticks.png
Iceane-3D-vdW.png
Names
IUPAC name
Tetracyclo[5.3.1.12,6.04,9]dodecane
Other names
Wurtzitane
Identifiers
3D model (JSmol)
ChemSpider
  • 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
  • C1C2CC3CC1C4CC2CC3C4
Properties
C12H18
Molar mass 163.56 g/mol
Structure
D3h
0 D
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

See alsoEdit

ReferencesEdit

  1. ^ Fieser, L. F. (1965). "Extensions in the use of plastic tetrahedral models". J. Chem. Educ. 42 (8): 408–412. doi:10.1021/ed042p408.
  2. ^ 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.
  3. ^ Tobler, H.; Klaus, R. O.; Ganter, C. (1975). "Wurtzitan (Tetracyclo[5.3.1.12,6.04,9]dodecan)". Helv. Chim. Acta. 58 (5): 1455–1464. doi:10.1002/hlca.19750580522.
  4. ^ Hamon, D. P. G.; Taylor, G. F. (1976). "A synthesis of tetracyclo[5,3,1,12,6,04,9]dodecane (iceane)". Aust. J. Chem. 29 (8): 1721–1734. doi:10.1071/CH9761721.

External linksEdit