Iceane
Encyclopedia
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 bonds.
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.
Polycyclic compound
In organic chemistry, a polycyclic compound is a cyclic compound with more than one hydrocarbon loop or ring structures . In general, the term includes all polycyclic aromatic compounds, including the polycyclic aromatic hydrocarbons, the heterocyclic aromatic compounds containing sulfur,...
hydrocarbon
Hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....
with formula C12H18. It has a cage
Cage (enclosure)
A cage is an enclosure made of mesh, bars or wires, used to confine, contain or protect something or someone. A cage can serve many purposes, including keeping an animal in captivity, capturing, and being used for display of an animal at a zoo.-History:...
-like molecular
Molecule
A molecule is an electrically neutral group of at least two atoms held together by covalent chemical bonds. Molecules are distinguished from ions by their electrical charge...
structure, whose carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
skeleton can be viewed as three fused cyclohexane
Cyclohexane
Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which being intermediates used in the production of nylon...
rings in the "boat" conformation
Cyclohexane conformation
A cyclohexane conformation is any of several three-dimensional shapes that a cyclohexane molecule can assume while maintaining the integrity of its chemical bonds....
; or as two such rings in the "chair" conformation, connected by three parallel bonds.
The name "iceane" was proposed by the chemist Louis Fieser
Louis Fieser
Louis Frederick Fieser was an organic chemist, professor, and in 1968, professor emeritus at Harvard University. He was renowned as the inventor, in 1943, of a militarily effective form of napalm...
about a decade before the compound was first prepared. He was carrying out studies on the arrangement of water
Water
Water is a chemical substance with the chemical formula H2O. A water molecule contains one oxygen and two hydrogen atoms connected by covalent bonds. Water is a liquid at ambient conditions, but it often co-exists on Earth with its solid state, ice, and gaseous state . Water also exists in a...
molecules in ice
Ice
Ice is water frozen into the solid state. Usually ice is the phase known as ice Ih, which is the most abundant of the varying solid phases on the Earth's surface. It can appear transparent or opaque bluish-white color, depending on the presence of impurities or air inclusions...
, when it occurred to him that there could exist a stable hydrocarbon with the above structure.