Iceane

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Iceane
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Names
IUPAC name
Tetracyclo[5.3.1.12,6.04,9]dodecane
Other names
Wurtzitane
Identifiers
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3D model (JSmol)
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  • 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 162.276 g·mol−1
Melting point 325 °C (617 °F; 598 K)[1]
Boiling point Sublimes[1]
Structure
D3h[2]
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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Iceane, colored by symmetry, Carbon in black and blue, hydrogen in white and cyan

Iceane is a saturated polycyclic hydrocarbon with formula Page Module:Chem2/styles.css has no content.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.

See also

References

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  1. ^ a b c Page Module:Citation/CS1/styles.css has no content.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.
  2. ^ Page Module:Citation/CS1/styles.css has no content.Cupas, Chris A.; Hodakowski, Leonard (July 1974). "Iceane". Journal of the American Chemical Society. 96 (14): 4668–4669. doi:10.1021/ja00821a050.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Fieser, L. F. (1965). "Extensions in the use of plastic tetrahedral models". J. Chem. Educ. 42 (8): 408–412. doi:10.1021/ed042p408.
  4. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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.
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