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Encyclopedia > Cyclopropane
Molecule structure formula of cyclopropane
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Molecule structure formula of cyclopropane

Cyclopropane is a cycloalkane molecule with the molecular formula C3H6 consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms. The bonds between the carbon atoms are a great deal weaker than in a typical carbon-carbon bond. This is the result of the 60° angle between the carbon atoms, which is far less than the normal angle of 109.5°. This ring strain has to be subtracted from the normal C-C bond energy, making the resultant compound more reactive than acyclic alkanes and other cycloalkanes such as cyclohexane and cyclopentane. This is the banana bond description of cycloalkanes. Image File history File links Molecule structure of Cyclopropane, typeset with PPCHTeX. startchemical chemical[THREE, SB,Z,-SR,+SR,-RZ,+RZ][C,C,C,H,H,H,H,H,H] stopchemical File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old... Image File history File links Molecule structure of Cyclopropane, typeset with PPCHTeX. startchemical chemical[THREE, SB,Z,-SR,+SR,-RZ,+RZ][C,C,C,H,H,H,H,H,H] stopchemical File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old... Cycloalkanes are chemical compounds with a one or more rings of carbons to which hydrogens are attached according to the formula CnH2n. ... In general, a molecule is the smallest particle of a pure chemical substance that still retains its composition and chemical properties. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... Properties For alternative meanings see atom (disambiguation). ... Italic textLink titleLink titlelink titlelink titleBold text General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... A chemical compound is a chemical substance formed from two or more elements, with a fixed ratio determining the composition. ... It has been suggested that List of alkanes be merged into this article or section. ... The term alicyclic compound refers to organic chemical compounds that are both aliphatic and cyclic. ... Cyclohexane is a molecule with the molecular formula C6H12 (molar mass = 84. ... Flash point -37 °C R/S statement R: ? S: ? RTECS number GY2390000 Supplementary data page Structure and properties n, εr, etc. ... Banana bonds or bent bonds are a special type of chemical bonding in which the ordinary hybridization state of two atoms making up a chemical bond are modified with increased or decreased s-orbital character in order to accommodate a particular molecular geometry. ...


However, cyclopropanes are more stable than a simple angle strain analysis would suggest. This is because the banana-bond model (without major tweaks) is incorrect; cyclopropane is better modeled as a three-center-bonded orbital combination of methylene carbenes. This results in the walsh orbital description of cyclopropane, where the C-C bonds have mostly pi character. This is also why cyclopropanes often have reactivity similar to alkenes. This is also why carbenes can easily add into alkenes to produce cyclopropanes. Banana bonds or bent bonds are a special type of chemical bonding in which the ordinary hybridization state of two atoms making up a chemical bond are modified with increased or decreased s-orbital character in order to accommodate a particular molecular geometry. ... In chemistry, a three-center bond is a type of covalent bond, in which one pair of electrons joins three atoms rather than the usual two. ... In chemistry a carbene is a short-lived and highly reactive organic molecule with a divalent carbon atom with only six valence electrons and the general formula: R1R2C:. The carbon atom is sp2 hybridised with an empty p-orbital extending above and below a plane containing R1 and R2 and... An alkene in organic chemistry is an unsaturated hydrocarbon containing at least one carbon to carbon double bond. ...


Boiling point: -32.8°C Freezing point: -127°C


The pyrethrum insecticides (found in certain Chrysanthemum species) contain a cyclopropane ring. Pyrethrum (Chrysanthemum cinerariaefolium, Family Asteraceae) is a perennial African plant with a daisy-like appearance and white, pink or red flowers. ... Pyrethrum (Chrysanthemum cinerariaefolium, Family Asteraceae) is a perennial African plant with a daisy-like appearance and white, pink or red flowers. ...


Cyclopropane is an anaesthetic when inhaled, but has been superseded by other agents in modern anaesthetic practice. This is due to its extreme reactivity under normal conditions: when the gas is mixed with oxygen there is a significant risk of explosion.


Because of the strain in the carbon-carbon bonds of cyclopropane, the molecule has an enormous amount of potential energy. In pure form, it will break down to form linear alkanes and alkenes, including "normal", non-cyclic propane. This decomposition is potentially explosive, especially if the cyclopropane is liquified, pressurized, or contained within tanks. Explosions of cyclopropane and oxygen are even more powerful, because the energy released by the formation of normal propane is compounded by the energy released via the oxidation of the carbon and hydrogen present. At room temperature, sufficent volumes of liquified cyclopropane will self-detonate. To guard against this, the liquid is shipped in cylinders filled with tungsten wool, which prevents high-speed collisions between molecules and vastly improves stability. Pipes to carry cyclopropane must likewise be of small diameter, or else filled with unreactive metal or glass wool, to prevent explosions. Even if these precautions are followed, cyclopropane is dangerous to handle and manufacture, and is no longer used for anaesthesia.


External links

  • Molview from bluerhinos.co.uk See Cyclopropane in 3D

  Results from FactBites:
 
Walsh Cyclopropane Molecular Orbitals (155 words)
Walsh Cyclopropane is a common topic in upper-level organic chemistry courses, particularly those taught by chemists who (like me) are fascinated by interesting ways of describing bonds.
Cyclopropane shows properties and reactivity consistent with π-type conjugation with neighboring carbocations and radicals.
The C-H force constants in cyclopropane are consistent with Walsh's assumption of sp
Cyclopropane - Drug information from Medic8.com (559 words)
Cyclopropane is a cycloalkane molecule with the molecular formula C3H6 consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms.
Explosions of cyclopropane and oxygen are even more powerful, because the energy released by the formation of normal propane is compounded by the energy released via the oxidation of the carbon and hydrogen present.
Cyclopropanes are a class of organic compounds sharing the common cyclopropyl functional group.
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