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Cyclophane
In organic chemistry, a cyclophane is a hydrocarbon consisting of an aromatic unit (typically a benzene ring) and a chain that forms a bridge between two non-adjacent positions of the aromatic ring. More complex derivatives with multiple aromatic units and bridges forming cagelike structures are also known. Cyclophanes are well-studied examples of strained organic compounds. Cyclophanes Structures Paracyclophanes adopt the boat conformation normally observed in cyclohexanes. Smaller value of n lead to greater distortions. X-ray crystallography on ' aracyclophane' shows that the aromatic bridgehead carbon atom makes an angle of 20.5° with the plane. The benzyl carbons deviate by another 20.2°. The carbon-to-carbon bond length alternation has increased from 0 for benzene to 39 pm. Despite their distorted structures, cyclophanes retain their aromaticity, as determined by UV-vis spectroscopy. Reactivity With regards to their reactivity, cyclophanes often exhibit diene-like ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Superphane
.2.2.2.2.21,2,3,4,5,6)Cyclophane or superphane is a 6-fold bridged cyclophane with all arene positions in the benzene dimer taken up by ethylene spacers. The compound has been of some scientific interest as a model for testing aromaticity and was first synthesised by Virgil Boekelheide in 1979. Superphane is the base compound for a large group of derivatives with structural variations. The analogs with 2 to 5 bridges are also known compounds. The benzene rings have been replaced by other aromatic units, such as those based on ferrocene or stabilized cyclobutadiene. Numerous derivatives are known with variations in the type and length of the bridging units. Synthesis The first synthesis of superphane itself by Boekelheide involved forming pairs of bridging units. At each stage, two ''o''-chloromethyl toluene structures are pyrolyzed to form ''o''-xylylenes, either directly or via benzocyclobutene intermediates. Upon further pyrolysis, these each undergo electrocyclic ring-opening ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dewar Benzene
Dewar benzene (also spelled ''dewarbenzene'') or bicyclo .2.0exa-2,5-diene is a bicyclic isomer of benzene with the molecular formula C6H6. The compound is named after James Dewar who included this structure in a list of possible C6H6 structures in 1869. However, he did not propose it as the structure of benzene, and in fact he supported the correct structure previously proposed by August Kekulé in 1865. Structure and properties Unlike benzene, Dewar benzene is not flat because the carbons where the rings join are bonded to four atoms rather than three. These carbons tend toward tetrahedral geometry, and the two cyclobutene rings make an angle where they are ''cis''- fused to each other. The compound has nevertheless considerable strain energy and reverts to benzene with a chemical half-life of two days. This thermal conversion is relatively slow because it is symmetry forbidden based on orbital symmetry arguments. Synthesis The compound itself was first synthesized in 1962 as ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Rearrangement Reaction
In organic chemistry, a rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. Often a substituent moves from one atom to another atom in the same molecule, hence these reactions are usually intramolecular. In the example below, the substituent R moves from carbon atom 1 to carbon atom 2: :\underset\ce\ce\underset\ce\ce Intermolecular rearrangements also take place. A rearrangement is not well represented by simple and discrete electron transfers (represented by curved arrows in organic chemistry texts). The actual mechanism of alkyl groups moving, as in Wagner-Meerwein rearrangement, probably involves transfer of the moving alkyl group fluidly along a bond, not ionic bond-breaking and forming. In pericyclic reactions, explanation by orbital interactions give a better picture than simple discrete electron transfers. It is, nevertheless, possible to draw the curv ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Silver Perchlorate
Silver perchlorate is the chemical compound with the formula AgClO4. This white solid forms a monohydrate and is mildly deliquescent. It is a useful source of the Ag+ ion, although the presence of perchlorate presents risks. It is used as a catalyst in organic chemistry. Production Silver perchlorate is created by heating a mixture of perchloric acid with silver nitrate. Alternatively, it can be prepared by the reaction between barium perchlorate and silver sulfate, or from the reaction of perchloric acid with silver oxide. Solubility Silver perchlorate is noteworthy for its solubility in aromatic solvents such as benzene (52.8 g/L) and toluene (1010 g/L). In these solvents, the silver cation binds to the arene, as has been demonstrated by extensive crystallographic studies on crystals obtained from such solutions. Its solubility in water is extremely high, up to 500 g per 100 mL water. Related reagents Similar to silver nitrate, silver perchlorate is an effective reagent fo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carbene
In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is or where the R represents substituents or hydrogen atoms. The term "carbene" may also refer to the specific compound , also called methylene, the parent hydride from which all other carbene compounds are formally derived. Carbenes are classified as either singlets or triplets, depending upon their electronic structure. Most carbenes are very short lived, although persistent carbenes are known. One well-studied carbene is dichlorocarbene , which can be generated ''in situ'' from chloroform and a strong base. Structures and bonding The two classes of carbenes are singlet and triplet carbenes. Singlet carbenes are spin-paired. In the language of valence bond theory, the molecule adopts an sp2 hybrid structure. Triplet carbenes have two unpaired electrons. Most carbenes have a nonlinear triplet ground state, e ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pyrolysis
The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''pyro'' "fire", "heat", "fever" and '' lysis'' "separating". Pyrolysis is most commonly used in the treatment of organic materials. It is one of the processes involved in charring wood.''Burning of wood'' , InnoFireWood's website. Accessed on 2010-02-06. In general, pyrolysis of organic substances produces volatile products and leaves , a carbon-rich solid residue. Extreme pyrolysis, which leaves mostly |
Ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' is methyl), with the formula . Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone. Nomenclature and etymology The word ''ketone'' is derived from ''Aketon'', an old German word for ''acetone''. According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix ''-ane'' of the parent alkane to ''-anone''. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considere ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Spiro Compound
In organic chemistry, spiro compounds are compounds that have at least two molecular rings with only one common atom. The simplest spiro compounds are bicyclic (having just two rings), or have a bicyclic portion as part of the larger ring system, in either case with the two rings connected through the defining single common atom. The one common atom connecting the participating rings distinguishes spiro compounds from other bicyclics: from ''isolated ring compounds'' like biphenyl that have no connecting atoms, from ''fused ring compounds'' like decalin having two rings linked by two adjacent atoms, and from ''bridged ring compounds'' like norbornane with two rings linked by two non-adjacent atoms.For all four categories, see The specific chapters can be found aan respectively, same access date. For the description featuring adjacent atoms for all but the isolated category, see Clayden, op. cit. Spiro compounds may be fully carbocyclic (all carbon) or heterocyclic (havi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
