Cyclopentane (also called C pentane) is a highly flammable alicyclic

hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...

with

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbol ...

C₅H₁₀ and

CAS number A CAS Registry Number (also referred to as CAS RN or informally CAS Number) is a unique identification number assigned by the Chemical Abstracts Service (CAS), US to every chemical substance described in the open scientific literature. It inclu ...

287-92-3, consisting of a ring of five

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon mak ...

atoms each bonded with two

hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic ...

atoms above and below the plane. It occurs as a colorless liquid with a

petrol Gasoline (; ) or petrol (; ) (see ) is a transparent, petroleum-derived flammable liquid that is used primarily as a fuel in most spark-ignited internal combustion engines (also known as petrol engines). It consists mostly of organic c ...

-like odor. Its

melting point The melting point (or, rarely, liquefaction point) of a substance is the temperature at which it changes state from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium. The melting point of a substance depen ...

is −94 °C and its boiling point is 49 °C. Cyclopentane is in the class of cycloalkanes, being alkanes that have one or more rings of carbon atoms. It is formed by cracking cyclohexane in the presence of alumina at a high temperature and pressure. It was first prepared in 1893 by the German chemist

Johannes Wislicenus Johannes Wislicenus (24 June 1835 – 5 December 1902) was a German chemist, most famous for his work in early stereochemistry. Biography The son of the radical Protestant theologian Gustav Wislicenus, Johannes was born on 24 June 1835 in K ...

Production, occurrence and use

Cycloalkanes are formed by

catalytic reforming Catalytic reforming is a chemical process used to convert petroleum refinery naphthas distilled from crude oil (typically having low octane ratings) into high-octane liquid products called reformates, which are premium blending stocks for high-oc ...

. For example, when passed over a hot platinum surfact, 2-methylbutane converts into cyclopentane. Cyclopentane has no particular use. No commercial products are made from cyclopentane itself. As a volatile hydrocarbon it is an incidental component of some fuels and

blowing agent A blowing agent is a substance which is capable of producing a cellular structure via a foaming process in a variety of materials that undergo hardening or phase transition, such as polymers, plastics, and metals. They are typically applied wh ...

s. In principle, it could be used as a refrigerant except that it is rather flammable. Cyclopentane can be fluorinated to give compounds ranging from to perfluorocyclopentane . Such species are conceivable refrigerants and specialty solvents. The cyclopentane ring is pervasive in natural products including many useful drugs. Examples include most steroids, prostaglandins, and some lipids.

Conformations

In a

regular pentagon In geometry, a pentagon (from the Greek πέντε ''pente'' meaning ''five'' and γωνία ''gonia'' meaning ''angle'') is any five-sided polygon or 5-gon. The sum of the internal angles in a simple pentagon is 540°. A pentagon may be simpl ...

the angles at the vertices are all 108°, slightly less than the bond angle in perfectly tetrahedrally bonded carbon, which is about 109.47°. But cyclopentane is not planar in its normal conformations. It puckers in order to increase the distances between the hydrogen atoms (something which does not happen in the planar

cyclopentadienyl anion In chemistry, the cyclopentadienyl anion or cyclopentadienide is an aromatic species with a formula of and abbreviated as Cp−. It is formed from the deprotonation of the molecule cyclopentadiene. Properties The cyclopentadienyl anion i ...

because it doesn't have as many hydrogen atoms). This means that the average C-C-C angle is less than 108°. There are two conformations that give local minima of the energy, the "envelope" and the "half-chair". The envelope has mirror symmetry ( C), while the half chair has two-fold rotational symmetry ( C). In both cases the symmetry implies that there are two pairs of equal C-C-C angles and one C-C-C angle that has no pair. In fact for cyclopentane, unlike for cyclohexane (C₆H₁₂, see

cyclohexane conformation In organic chemistry, cyclohexane conformations are any of several three-dimensional shapes adopted by molecules of cyclohexane. Because many compounds feature structurally similar six-membered rings, the structure and dynamics of cyclohexane ...

) and higher cycloalkanes, it is not possible geometrically for all the angles and bond lengths to be equal except if it is in the form of a flat regular pentagon. File:Cyclopentane envelope conformation.svg, Envelope File:Cyclopentane3D.png, 3D envelope File:Cyclopentane halfchair.svg, Half-chair

References

External links

* {{Authority control Cyclopentanes Hydrocarbon solvents Cycloalkanes