Iceane

Chembox new
Name = Iceane
ImageFileL1 = Iceane-3D-sticks.png ImageSizeL1 = 100px
ImageFileR1 = Iceane-3D-vdW.png ImageSizeR1 = 100px
IUPACName = Tetracyclo [5.3.1.1^2,60^4,9] dodecane
OtherNames = Iceane
Section1 = Chembox Identifiers
SMILES = C1C2CC3CC1C1CC2CC3C1
CASNo = 53283-19-5
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InChI= 1/C12H18/c1-7-2-11-3-8(1)10-4-9(7)5- 12(11)6-10/h7-12H,1-6H2
Section2 = Chembox Properties
Formula = C₁₂H₁₈
MolarMass = 163.56 g/mol
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Section3 = Chembox Structure
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Section7 = Chembox Hazards
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Iceane (C₁₂H₁₈) is a saturated hydrocarbon variant of adamantane. The structure of iceane resembles a cage formed by three fused boat cyclohexanes - or alternately two chair cyclohexanes connected by three axial bonds. Its name 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 the three vertical hexagons with boat conformations, linked by three equatorial hydrogen bonds, could indicate the existence of a stable hydrocarbon counterpart. This gave rise to the name iceane which refers to the fact that it resembles the shape of ice.

External links

* [http://www.rsc.org/publishing/journals/article.asp?doi=C39820000372 Royal Society of Chemistry Journal]
* [http://books.google.co.uk/books?id=U-VW1MPrX0UC&pg=PA129&lpg=PA129&dq=iceane&source=web&ots=rDYPei2_Rx&sig=utmV9O3nTJcYeyEP8DJDRHW87a0&hl=en#PPA129,M1 "Symmetry Through the Eyes of a Chemist", Magdolna Hargittai]
* [http://books.google.com/books?id=7kvAOwqRU0sC&pg=PA68&dq=iceane&ei=COHTR_32IJGgygTghPyABA&sig=u38TtPLJfOn1kO8X4FQ9Ph-5-KI#PPA68,M1Symmetry: "A Basis for Synthesis Design", Tse-Lok Ho]
* [http://books.google.co.uk/books?id=2sSMEMkarFkC&pg=PA154&lpg=PA154&dq=iceane+CAS+rn&source=web&ots=C1kQeVJ9IQ&sig=JiACJW1L595tHxO9a91NSP_lqF4&hl=en#PPA154,M1 "Structures and Energies of Polycyclic Hydrocarbons", Joan E. Shields]