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Cyclooctene
Cyclooctene is the cycloalkene with a formula . Its molecule has a ring of 8 carbon atoms, connected by seven single bonds and one double bond. Cyclooctene is notable because it is the smallest cycloalkene that can exist stably as either the cis–trans isomerism, ''cis'' or ''trans'' stereoisomer, with cis-Cyclooctene, ''cis''-cyclooctene being the most common. Theoretical analysis implies a total of 16 Conformational isomerism, conformational and molecular configuration, configurational isomers, all chiral, forming 8 enantiomer, enantiomeric pairs. The ''cis'' isomer can adopt various conformations, the most stable one being shaped like a ribbon. The most stable conformation of trans-Cyclooctene, ''trans''-cyclooctene is shaped like the 8-carbon equivalent of the chair conformation of cyclohexane. Longer cycloalkene rings such as the ten-carbon cyclodecene also occur as ''cis'' and ''trans'' isomers. References External links *{{Commonscatinline Cycloalkenes Eight-mem ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cis-Cyclooctene
''cis''-Cyclooctene is a cycloalkene with the formula (CH2)6(CH)2. It is a colorless liquid that is used industrially to produce a polymer. It is also a ligand in organometallic chemistry. Cyclooctene is the smallest cycloalkene that can be isolated as both the ''cis''- and ''trans''-isomer. ''cis''-Cyclooctene is shaped like the 8-carbon equivalent chair conformation of cyclohexane. Uses and reactions Cyclooctene undergoes ring-opening metathesis polymerization to give polyoctenamers, which are marketed under the name Vestenamer. ''cis''-Cyclooctene (COE) is a substrate known for quite selectively forming the epoxide, as compared to other cycloalkenes, e.g. cyclohexene. Low amounts of radical by-products are found only. This behaviour is attributed to the difficulty of functionalizing allylic CH centers, which almost orthogonal allylic C-H bonds. Therefore, if radicals are around, they tend to form epoxide via an addition-elimination mechanism. It is used as an easily di ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Trans-Cyclooctene
''trans''-Cyclooctene is a cyclic hydrocarbon with the formula (CH2)6CH=CH– where the two C–C single bonds adjacent to the double bond are on opposite sides of the latter's plane. It is a colorless liquid with a disagreeable odor. Cyclooctene is notable as the smallest cycloalkene that is readily isolated as its ''trans''- isomer. The ''cis''-isomer is much more stable; the ring-strain energies being 16.7 and 7.4 kcal/mol, respectively.Ron Walker, Rosemary M. Conrad, and Robert H. Grubbs (2009): "The living ROMP of ''trans''-cyclooctene". ''Macromolecules'', volume 42, issue 3, pages 599–605. A planar arrangement of the ring carbons would be too strained, and therefore the stable conformations of the ''trans'' form have a bent (non-planar) ring. Computations indicate that the most stable "crown" conformation has the carbon atoms alternately above and below the plane of the ring. A "half-chair" conformation, with about 6 kcal/mol higher energy, has carbons 2,3,5, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclooctene Isomers Structural Formulae
Cyclooctene is the cycloalkene with a formula . Its molecule has a ring of 8 carbon atoms, connected by seven single bonds and one double bond. Cyclooctene is notable because it is the smallest cycloalkene that can exist stably as either the ''cis'' or ''trans'' stereoisomer, with ''cis''-cyclooctene being the most common. Theoretical analysis implies a total of 16 conformational and configurational isomers, all chiral, forming 8 enantiomeric pairs. The ''cis'' isomer can adopt various conformations, the most stable one being shaped like a ribbon. The most stable conformation of ''trans''-cyclooctene is shaped like the 8-carbon equivalent of the chair conformation of cyclohexane. Longer cycloalkene rings such as the ten-carbon cyclodecene Cyclodecene is a cycloalkene with a ten-membered ring, with two possible geometric isomers Geometry (; ) is, with arithmetic, one of the oldest branches of mathematics. It is concerned with properties of space such as the dist ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cycloalkene
A cycloalkene or cycloolefin is a type of alkene hydrocarbon which contains a closed ring of carbon atoms and either one or more double bonds, but has no aromatic character. Some cycloalkenes, such as cyclobutene and cyclopentene, can be used as monomers to produce polymer chains. Due to geometrical considerations, smaller cycloalkenes are almost always the ''cis'' isomers, and the term ''cis'' tends to be omitted from the names. Cycloalkenes require considerable p-orbital overlap in the form of a bridge between the carbon-carbon double bond, however, this is not feasible in smaller molecules due to the increase of strain that could break the molecule apart. In greater carbon number cycloalkenes, the addition of CH2 substituents decreases strain. trans-Cycloalkenes with 7 or fewer carbons in the ring will not occur under normal conditions because of the large amount of ring strain needed. In larger rings (8 or more atoms), ''cis''–''trans'' isomerism of the double bond may occur ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cycloalkenes
A cycloalkene or cycloolefin is a type of alkene hydrocarbon which contains a closed ring of carbon atoms and either one or more double bonds, but has no aromatic character. Some cycloalkenes, such as cyclobutene and cyclopentene, can be used as monomers to produce polymer chains. Due to geometrical considerations, smaller cycloalkenes are almost always the ''cis'' isomers, and the term ''cis'' tends to be omitted from the names. Cycloalkenes require considerable p-orbital overlap in the form of a bridge between the carbon-carbon double bond, however, this is not feasible in smaller molecules due to the increase of strain that could break the molecule apart. In greater carbon number cycloalkenes, the addition of CH2 substituents decreases strain. trans-Cycloalkenes with 7 or fewer carbons in the ring will not occur under normal conditions because of the large amount of ring strain needed. In larger rings (8 or more atoms), ''cis''–''trans'' isomerism of the double bond may occur ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 makes up only about 0.025 percent of Earth's crust. Three isotopes occur naturally, C and C being stable, while C is a radionuclide, decaying with a half-life of about 5,730 years. Carbon is one of the few elements known since antiquity. Carbon is the 15th most abundant element in the Earth's crust, and the fourth most abundant element in the universe by mass after hydrogen, helium, and oxygen. Carbon's abundance, its unique diversity of organic compounds, and its unusual ability to form polymers at the temperatures commonly encountered on Earth, enables this element to serve as a common element of all known life. It is the second most abundant element in the human body by mass (about 18.5%) after oxygen. The atoms of carbo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Single Bond
In chemistry, a single bond is a chemical bond between two atoms involving two valence electrons. That is, the atoms share one pair of electrons where the bond forms. Therefore, a single bond is a type of covalent bond. When shared, each of the two electrons involved is no longer in the sole possession of the orbital in which it originated. Rather, both of the two electrons spend time in either of the orbitals which overlap in the bonding process. As a Lewis structure, a single bond is denoted as AːA or A-A, for which A represents an element. In the first rendition, each dot represents a shared electron, and in the second rendition, the bar represents both of the electrons shared in the single bond. A covalent bond can also be a double bond or a triple bond. A single bond is weaker than either a double bond or a triple bond. This difference in strength can be explained by examining the component bonds of which each of these types of covalent bonds consists (Moore, Stanitsk ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Double Bond
In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist between two different elements: for example, in a carbonyl group between a carbon atom and an oxygen atom. Other common double bonds are found in azo compounds (N=N), imines (C=N), and sulfoxides (S=O). In a skeletal formula, a double bond is drawn as two parallel lines (=) between the two connected atoms; typographically, the equals sign is used for this. Double bonds were first introduced in chemical notation by Russian chemist Alexander Butlerov. Double bonds involving carbon are stronger and shorter than single bonds. The bond order is two. Double bonds are also electron-rich, which makes them potentially more reactive in the presence of a strong electron acceptor (as in addition reactions of the halogens). File:Ethene structural.svg, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cis–trans Isomerism
''Cis''–''trans'' isomerism, also known as geometric isomerism or configurational isomerism, is a term used in chemistry that concerns the spatial arrangement of atoms within molecules. The prefixes "''cis''" and "''trans''" are from Latin: "this side of" and "the other side of", respectively. In the context of chemistry, ''cis'' indicates that the functional groups (substituents) are on the same side of some plane, while ''trans'' conveys that they are on opposing (transverse) sides. ''Cis''–''trans'' isomers are stereoisomers, that is, pairs of molecules which have the same formula but whose functional groups are in different orientations in three-dimensional space. ''Cis-trans'' notation does not always correspond to ''E''–''Z'' isomerism, which is an ''absolute'' stereochemical description. In general, ''cis''–''trans'' stereoisomers contain double bonds that do not rotate, or they may contain ring structures, where the rotation of bonds is restricted or prevented ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Stereoisomer
In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space. This contrasts with structural isomers, which share the same molecular formula, but the bond connections or their order differs. By definition, molecules that are stereoisomers of each other represent the same structural isomer. Enantiomers Enantiomers, also known as optical isomers, are two stereoisomers that are related to each other by a reflection: they are mirror images of each other that are non-superposable. Human hands are a macroscopic analog of this. Every stereogenic center in one has the opposite configuration in the other. Two compounds that are enantiomers of each other have the same physical properties, except for the direction in which they rotate polarized light and how they interact with different optical isomers ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Conformational Isomerism
In chemistry, conformational isomerism is a form of stereoisomerism in which the isomers can be interconverted just by rotations about formally single bonds (refer to figure on single bond rotation). While any two arrangements of atoms in a molecule that differ by rotation about single bonds can be referred to as different conformations, conformations that correspond to local minima on the potential energy surface are specifically called conformational isomers or conformers. Conformations that correspond to local maxima on the energy surface are the transition states between the local-minimum conformational isomers. Rotations about single bonds involve overcoming a rotational energy barrier to interconvert one conformer to another. If the energy barrier is low, there is free rotation and a sample of the compound exists as a rapidly equilibrating mixture of multiple conformers; if the energy barrier is high enough then there is restricted rotation, a molecule may exist for a r ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Molecular Configuration
The molecular configuration of a molecule is the ''permanent'' geometry that results from the spatial arrangement of its bonds. The ability of the same set of atoms to form two or more molecules with different configurations is stereoisomerism. Used as drugs, compounds with different configuration normally have ''different'' physiological activity, including the desired pharmacological effect, the toxicology and the metabolism.Everhardus Ariëns: ''Stereochemistry, the basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology'', European Journal of Clinical Pharmacology 26 (1984) 663-668, . Configuration is distinct from chemical conformation, a shape attainable by bond rotations. See also * Absolute configuration Absolute configuration refers to the spatial arrangement of atoms within a chiral molecular entity (or group) and its resultant stereochemical description. Absolute configuration is typically relevant in organic molecules, where carbon is bo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
