Arsaalkyne
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Arsaalkyne
In chemistry, an arsaalkyne is chemical compound with a triple bond between carbon and arsenic. These organoarsenic compounds are rare, especially in comparison with the phosphaalkynes. The parent HCAs has been characterized spectroscopically, otherwise the only arsaalkynes have bulky organic substituents. Synthesis and isolation Arsaalkynes are produced by dehydrohalogenation or related base-induced elimination reactions. The case of HCAs is illustrative: : Owing to the principles of the double bond rule, arsaalkynes tend to oligomerize more readily than the phosphorus analogues. Thus attempts to prepare AsCCMe3 produce the tetramer, which has a cubane Cubane () is a synthetic hydrocarbon compound that consists of eight carbon atoms arranged at the corners of a cube, with one hydrogen atom attached to each carbon atom. A solid crystalline substance, cubane is one of the Platonic hydrocarbons an ... structure. The very bulky substituent C6H2-2,4,6-(''t''-Bu)3 does however ...
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Phosphaalkyne
In chemistry, a phosphaalkyne (IUPAC name: alkylidynephosphane) is an organophosphorus compound containing a triple bond between phosphorus and carbon with the general formula R-C≡P. Phosphaalkynes are the heavier congeners of nitriles, though, due to the similar electronegativities of phosphorus and carbon, possess reactivity patterns reminiscent of alkynes. Due to their high reactivity, phosphaalkynes are not found naturally on earth, but the simplest phosphaalkyne, phosphaethyne (H-C≡P) has been observed in the interstellar medium. Synthesis From phosphine gas The first of preparation of a phosphaalkyne was achieved in 1961 when Thurman Gier produced phosphaethyne by passing phosphine gas at low pressure over an electric arc produced between two carbon electrodes. Condensation of the gaseous products in a –196 °C (–321 °F) trap revealed that the reaction had produced acetylene, ethylene, phosphaethyne, which was identified by infrared spectroscopy. By eliminatio ...
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Chemistry
Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds made of atoms, molecules and ions: their composition, structure, properties, behavior and the changes they undergo during a Chemical reaction, reaction with other Chemical substance, substances. Chemistry also addresses the nature of chemical bonds in chemical compounds. In the scope of its subject, chemistry occupies an intermediate position between physics and biology. It is sometimes called the central science because it provides a foundation for understanding both Basic research, basic and Applied science, applied scientific disciplines at a fundamental level. For example, chemistry explains aspects of plant growth (botany), the formation of igneous rocks (geology), how atmospheric ozone is formed and how environmental pollutants are degraded (ecology), the properties ...
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Triple Bond
A triple bond in chemistry is a chemical bond between two atoms involving six bonding electrons instead of the usual two in a covalent single bond. Triple bonds are stronger than the equivalent single bonds or double bonds, with a bond order of three. The most common triple bond, that between two carbon atoms, can be found in alkynes. Other functional groups containing a triple bond are cyanides and isocyanides. Some diatomic molecules, such as dinitrogen and carbon monoxide, are also triple bonded. In skeletal formulae the triple bond is drawn as three parallel lines (≡) between the two connected atoms. Bonding The types of bonding can be explained in terms of orbital hybridization. In the case of acetylene each carbon atom has two sp-orbitals and two p-orbitals. The two sp-orbitals are linear with 180° angles and occupy the x-axis ( cartesian coordinate system). The p-orbitals are perpendicular on the y-axis and the z-axis. When the carbon atoms approach each other, ...
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Arsenic
Arsenic is a chemical element with the symbol As and atomic number 33. Arsenic occurs in many minerals, usually in combination with sulfur and metals, but also as a pure elemental crystal. Arsenic is a metalloid. It has various allotropes, but only the gray form, which has a metallic appearance, is important to industry. The primary use of arsenic is in alloys of lead (for example, in car batteries and ammunition). Arsenic is a common n-type dopant in semiconductor electronic devices. It is also a component of the III-V compound semiconductor gallium arsenide. Arsenic and its compounds, especially the trioxide, are used in the production of pesticides, treated wood products, herbicides, and insecticides. These applications are declining with the increasing recognition of the toxicity of arsenic and its compounds. A few species of bacteria are able to use arsenic compounds as respiratory metabolites. Trace quantities of arsenic are an essential dietary element in rats, ham ...
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Organoarsenic Compound
Organoarsenic chemistry is the chemistry of compounds containing a chemical bond between arsenic and carbon. A few organoarsenic compounds, also called "organoarsenicals," are produced industrially with uses as insecticides, herbicides, and fungicides. In general these applications are declining in step with growing concerns about their impact on the environment and human health. The parent compounds are arsane and arsenic acid. Despite their toxicity, organoarsenic biomolecules are well known. History 140px, Cacodyl (tetramethyldiarsine) was one of the first organoarsenic compounds. Surprising for an area now considered of minor importance, organoarsenic chemistry played a prominent role in the history of the field of chemistry. The oldest known organoarsenic compound, the foul smelling cacodyl was reported in "cacodyl" (1760) and is sometimes classified as the first synthetic organometallic compound. The compound Salvarsan was one of the first pharmaceuticals, earning a Nobel ...
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Dehydrohalogenation
In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogenation from alkyl halides Traditionally, alkyl halides are substrates for dehydrohalogenations. The alkyl halide must be able to form an alkene, thus halides having no C–H bond on an adjacent carbon are not suitable substrates. Aryl halides are also unsuitable. Upon treatment with strong base, chlorobenzene dehydrohalogenates to give phenol via a benzyne intermediate. Base-promoted reactions to alkenes When treated with a strong base many alkyl chlorides convert to corresponding alkene. It is also called a β-elimination reaction and is a type of elimination reaction. Some prototypes are shown below: :\begin \ce\ &\ce \\ \ce\ &\ce \\ \ce\ &\ce \end Here ethyl chloride reacts with potassium hydroxide, typically in a solvent such as ethanol, giving ethylene. Li ...
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Elimination Reaction
An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction. The numbers refer not to the number of steps in the mechanism, but rather to the kinetics of the reaction: E2 is bimolecular (second-order) while E1 is unimolecular (first-order). In cases where the molecule is able to stabilize an anion but possesses a poor leaving group, a third type of reaction, E1CB, exists. Finally, the pyrolysis of xanthate and acetate esters proceed through an "internal" elimination mechanism, the Ei mechanism. E2 mechanism The E2 mechanism, where E2 stands for bimolecular elimination, involves a one-step mechanism in which ''carbon-hydrogen'' and ''carbon-halogen'' bonds break to form a double bond (''C=C Pi bond''). The specifics of the reaction are as follows: * E2 is a single step elimination, ...
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Double Bond Rule
In chemistry, the double bond rule states that elements with a principal quantum number greater than 2 for their valence electrons (period 3 elements and higher) tend not to form multiple bonds (e.g. double bonds and triple bonds). The double bonds, when they exist, are often weak due to poor orbital overlap. Although such compounds are not intrinsically unstable, they instead tend to polymerize. An example is the rapid polymerization that occurs upon condensation of disulfur, the heavy analogue of . Numerous violations to the rule exist. Other meanings Another unrelated double bond rule exists that relates to the enhanced reactivity of sigma bonds attached to an atom adjacent to a double bond. In bromoalkenes, the C–Br bond is very stable, but in an allyl bromide, this bond is very reactive. Likewise, bromobenzenes are generally inert, whereas benzylic bromides are reactive. The first to observe the phenomenon was Conrad Laar Conrad Peter Laar (22 March 1853 – 11 Fe ...
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Oligomer
In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relative molecular mass, the structure of which essentially comprises a small plurality of units derived, actually or conceptually, from molecules of lower relative molecular mass.'' The name is composed of Greek elements '' oligo-'', "a few" and '' -mer'', "parts". An adjective form is ''oligomeric''. The oligomer concept is contrasted to that of a polymer, which is usually understood to have a large number of units, possibly thousands or millions. However, there is no sharp distinction between these two concepts. One proposed criterion is whether the molecule's properties vary significantly with the removal of one or a few of the units. An oligomer with a specific number of units is referred to by the Greek prefix denoting that number, wi ...
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Tetramer
A tetramer () (''tetra-'', "four" + '' -mer'', "parts") is an oligomer formed from four monomers or subunits. The associated property is called ''tetramery''. An example from inorganic chemistry is titanium methoxide with the empirical formula Ti(OCH3)4, which is tetrameric in solid state and has the molecular formula Ti4(OCH3)16. An example from organic chemistry is kobophenol A, a substance that is formed by combining four molecules of resveratrol. In biochemistry, it similarly refers to a biomolecule formed of four units, that are the same (homotetramer), i.e. as in Concanavalin A or different (heterotetramer), i.e. as in hemoglobin. Hemoglobin has 4 similar sub-units while immunoglobulins have 2 very different sub-units. The different sub-units may have each their own activity, such as binding biotin in avidin tetramers, or have a common biological property, such as the allosteric binding of oxygen in hemoglobin. See also * Cluster chemistry; atomic and molecular clusters ...
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Cubane
Cubane () is a synthetic hydrocarbon compound that consists of eight carbon atoms arranged at the corners of a cube, with one hydrogen atom attached to each carbon atom. A solid crystalline substance, cubane is one of the Platonic hydrocarbons and a member of the prismanes. It was first synthesized in 1964 by Philip Eaton and Thomas Cole. Before this work, Eaton believed that cubane would be impossible to synthesize due to the "required 90 degree bond angles". The cubic shape requires the carbon atoms to adopt an unusually sharp 90° bonding angle, which would be highly strained as compared to the 109.45° angle of a tetrahedral carbon. Once formed, cubane is quite kinetically stable, due to a lack of readily available decomposition paths. It is the simplest hydrocarbon with octahedral symmetry. Having high potential energy but kinetic stability makes cubane and its derivative compounds useful for controlled energy storage. For example, octanitrocubane and heptanitrocubane have ...
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