|
Polyyne
In organic chemistry, a polyyne () is any organic compound with alternating single and triple bonds; that is, a series of consecutive alkynes, with ''n'' greater than 1. These compounds are also called polyacetylenes, especially in the natural products and chemical ecology literature, even though this nomenclature more properly refers to acetylene polymers composed of alternating single and double bonds with ''n'' greater than 1. They are also sometimes referred to as oligoynes, or carbinoids after " carbyne" , the hypothetical allotrope of carbon that would be the ultimate member of the series. In ''Avancés récentes en chimie des acétylènes – Recent advances in acetylene chemistry'' The synthesis of this substance has been claimed several times since the 1960s, but those reports have been disputed. Indeed, the substances identified as short chains of "carbyne" in many early organic synthesis attempts would be called polyynes today. The simplest polyyne is diacetylene ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Linear Acetylenic Carbon
Linear acetylenic carbon (LAC), also known as carbyne or Linear Carbon Chain (LCC), is an allotrope of carbon that has the chemical structure as a repeat unit, with alternating single and triple bonds. It would thus be the ultimate member of the polyyne family. This polymeric carbyne is of considerable interest to nanotechnology as its Young's modulus is – forty times that of diamond; this extraordinary number is, however, based on a novel definition of cross-sectional area that does not correspond to the space occupied by the structure. Carbyne has also been identified in interstellar space; however, its existence in condensed phases has been contested recently, as such chains would crosslink exothermically (and perhaps explosively) if they approached each other. History and controversy The first claims of detection of this allotrope were made in 1960Sladkov A.M, Kudryavtsev Y.P Diamond, graphite, carbyne 3/4 the allotropic forms of carbon, Priroda (Nature), 1969, 58:3 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Copper(I) Acetylide
Copper(I) acetylide, or cuprous acetylide, is a chemical compound with the formula Cu2 C2. Although never characterized by X-ray crystallography, the material has been claimed at least since 1856. One form is claimed to be a monohydrate with formula .. It is a reddish solid, that easily explodes when dry. Synthesis Materials purported to be copper acetylide can be prepared by treating acetylene with a solution of copper(I) chloride and ammonia: :C2H2 (g) + 2 CuCl (s) → Cu2C2 (s) + 2 HCl (g) This reaction produces a reddish solid precipitate. Properties When dry, copper acetylide is a heat and shock sensitive high explosive, more thermally sensitive than silver acetylide. Copper acetylide is thought to form inside pipes made of copper or an alloy with high copper content, which may result in violent explosion. This was found to be the cause of explosions in acetylene plants, and led to abandonment of copper as a construction material in such plants. Copper catalysts used ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Polyacetylene
Polyacetylene (IUPAC name: polyethyne) usually refers to an organic polymer with the repeating unit . The name refers to its conceptual construction from polymerization of acetylene to give a chain with repeating olefin groups. This compound is conceptually important, as the discovery of polyacetylene and its high conductivity upon doping helped to launch the field of organic conductive polymers. The high electrical conductivity discovered by Hideki Shirakawa, Alan Heeger, and Alan MacDiarmid for this polymer led to intense interest in the use of organic compounds in microelectronics ( organic semiconductors). This discovery was recognized by the Nobel Prize in Chemistry in 2000. Early work in the field of polyacetylene research was aimed at using doped polymers as easily processable and lightweight "plastic metals". Despite the promise of this polymer in the field of conductive polymers, many of its properties such as instability to air and difficulty with processing have ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Fritsch–Buttenberg–Wiechell Rearrangement
The Fritsch–Buttenberg–Wiechell rearrangement, named for Paul Ernst Moritz Fritsch (1859–1913), Wilhelm Paul Buttenberg, and Heinrich G. Wiechell, is a chemical reaction whereby a 1,1-diaryl-2-bromo-alkene rearranges to a 1,2-diaryl-alkyne by reaction with a strong base such as an alkoxide. This rearrangement is also possible with alkyl substituents. Reaction mechanism The strong base deprotonates the vinylic hydrogen, which after alpha-elimination forms a vinyl carbene. A 1,2-aryl migration forms the 1,2-diaryl-alkyne product. The mechanism of the FBW rearrangement was a subject of on-surface studies where the vinyl radical was visualised with sub-atomic resolution. Scope One study explored this reaction for the synthesis of novel polyynes:The metal acetylide intermediate is captured by electrophile methyl iodide. The reaction product is a biomolecule found in for instance Bidens pilosa ''Bidens pilosa'' is an annual species of herbaceous flowering plant in th ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cumulene
In organic chemistry, a cumulene is a compound having three or more ''cumulative'' (consecutive) double bonds. They are analogous to allenes, only having a more extensive chain. The simplest molecule in this class is butatriene (), which is also called simply ''cumulene''. Unlike most alkanes and alkenes, cumulenes tend to be rigid, comparable to polyynes. Cumulene carbenes for ''n'' from 3 to 6 have been observed in interstellar molecular clouds and in laboratory experiments by using microwave and infrared spectroscopy. (The more stable cumulenes are difficult to detect optically because they lack an electric dipole moment.) Cumulenes containing heteroatoms are called heterocumulenes; an example is carbon suboxide. Synthesis The first reported synthesis of a butatriene is that of tetraphenylbutatriene in 1921. The most common synthetic method for butatriene synthesis is based on reductive coupling of a geminal dihalo vinylidene. Tetraphenylbutatriene was reported sy ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diacetylene
Diacetylene (also known as butadiyne) is the organic compound with the formula C4H2. It is the simplest compound containing two triple bonds. It is first in the series of polyynes, which are of theoretical but not of practical interest. Occurrence Diacetylene has been identified in the atmosphere of Titan and in the protoplanetary nebula CRL 618 by its characteristic vibrational spectrum. It is proposed to arise by a reaction between acetylene and the ethynyl radical (C2H), which is produced when acetylene undergoes photolysis. This radical can in turn attack the triple bond in acetylene and react efficiently even at low temperatures. Diacetylene has also been detected on the Moon. Preparation This compound may be made by the dehydrohalogenation of 1,4-dichloro-2-butyne by potassium hydroxide (in alcoholic medium) at ~70°C: : ClCH2C#CCH2Cl + 2 KOH -> HC#C-C#CH + 2 KCl + 2 H2O The bis(trimethylsilyl)-protected derivative may be prepared by the Hay coupling of (trime ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ichthyothereol Skeletal
Ichthyothereol is a toxic polyyne compound found in the leaves and flowers of several plants in South and Central America. These plant sources and their extracts are known for their toxic effects on fish, and have long been used by various native tribes in the lower Amazon basin for fishing. The name of the genus '' Ichthyothere'', the members of which contain noticeable amounts of the natural product in their leaves, literally translates as ''fish poison.'' It is so toxic, fish will jump out of the water if ''Ichthyothere terminalis'' leaves are used as bait. This chemical is also found in the leaves and flowers of '' Dahlia coccinea''. The actual chemical was isolated by several different groups and its full chemical structure determined in 1965. The first total synthesis was published in 2001. It is also toxic to mice and dogs, producing convulsant effects that are similar to those of picrotoxin Picrotoxin, also known as cocculin, is a poisonous crystalline plant compound. It ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acetylene
Acetylene ( systematic name: ethyne) is the chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure form and thus is usually handled as a solution. Pure acetylene is odorless, but commercial grades usually have a marked odor due to impurities such as divinyl sulfide and phosphine.Compressed Gas Association (1995Material Safety and Data Sheet – Acetylene As an alkyne, acetylene is unsaturated because its two carbon atoms are bonded together in a triple bond. The carbon–carbon triple bond places all four atoms in the same straight line, with CCH bond angles of 180°. Discovery Acetylene was discovered in 1836 by Edmund Davy, who identified it as a "new carburet of hydrogen". It was an accidental discovery while attempting to isolate potassium metal. By heating potassium carbonate with carbon at very high temperatures, he pro ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ethyl Group
In organic chemistry, an ethyl group (abbr. Et) is an alkyl substituent with the formula , derived from ethane (). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry's nomenclature of organic chemistry for a saturated two-carbon moiety in a molecule, while the prefix "''eth-''" is used to indicate the presence of two carbon atoms in the molecule. Ethylation Ethylation is the formation of a compound by introduction of the ethyl group. The most widely practiced example of this reaction is the ethylation of benzene with ethylene to yield ethylbenzene, a precursor to styrene, which is a precursor to polystyrene. Approximately 24.7 million tons of ethylbenzene were produced in 1999. :: Many ethyl-containing compounds are generated by electrophilic ethylation, i.e. treatment of nucleophiles with sources of Et+. Triethyloxonium tetrafluoroborate t3OF4 is such a reagent. For good nucleophiles, less electrophilic reagents are employed, such as ethyl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alkyne
\ce \ce Acetylene \ce \ce \ce Propyne \ce \ce \ce \ce 1-Butyne In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula . Alkynes are traditionally known as acetylenes, although the name ''acetylene'' also refers specifically to , known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic. Structure and bonding In acetylene, the H–C≡C bond angles are 180°. By virtue of this bond angle, alkynes are rod-like. Correspondingly, cyclic alkynes are rare. Benzyne cannot be isolated. The C≡C bond distance of 121 picometers is much shorter than the C=C distance in alkenes (134 pm) or the C–C bond in alkanes (153 pm). : The triple bond is very strong with a bond strength of 839 kJ/mol. The sigma bond contri ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tris(3,5-di-t-butylphenyl)methyl
Tris, or tris(hydroxymethyl)aminomethane, or known during medical use as tromethamine or THAM, is an organic compound with the formula (HOCH2)3CNH2, one of the twenty Good's buffers. It is extensively used in biochemistry and molecular biology as a component of buffer solutions such as in TAE and TBE buffers, especially for solutions of nucleic acids. It contains a primary amine and thus undergoes the reactions associated with typical amines, e.g. condensations with aldehydes. Tris also complexes with metal ions in solution. In medicine, tromethamine is occasionally used as a drug, given in intensive care for its properties as a buffer for the treatment of severe metabolic acidosis in specific circumstances. Some medications are formulated as the "tromethamine salt" including Hemabate (carboprost as trometamol salt), and "ketorolac trometamol". Buffering features The conjugate acid of tris has a p''K''a of 8.07 at 25 °C, which implies that the buffer has an effective pH ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phenyl
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a functional group. Phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring. Nomenclature Usually, a "phenyl group" is synonymous with C6H5− and is represented by the symbol Ph or, archaically, Φ. Benzene is sometimes denoted as PhH. Phenyl groups are generally attached to other atoms or groups. For example, triphenylmethane ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
