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Acetylide
In organometallic chemistry, acetylide refers to chemical compounds with the chemical formulas and , where M is a metal. The term is used loosely and can refer to substituted acetylides having the general structure (where R is an organic side chain). Acetylides are reagents in organic synthesis. The calcium acetylide commonly called calcium carbide is a major compound of commerce. Structure and bonding Alkali metal and alkaline earth metal acetylides of the general formula MC≡CM are salt-like Zintl phase compounds, containing ions. Evidence for this ionic character can be seen in the ready hydrolysis of these compounds to form acetylene and metal oxides, there is also some evidence for the solubility of ions in liquid ammonia. The ion has a closed shell ground state of 1Σ, making it isoelectronic to a neutral molecule N2, which may afford it some stability. Analogous acetylides prepared from other metals, particularly transition metals, show covalent character and are ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Copper 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] |
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 produced a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Calcium Carbide
Calcium carbide, also known as calcium acetylide, is a chemical compound with the chemical formula of Ca C2. Its main use industrially is in the production of acetylene and calcium cyanamide. The pure material is colorless, while pieces of technical-grade calcium carbide are grey or brown and consist of about 80–85% of CaC2 (the rest is CaO (calcium oxide), Ca3P2 (calcium phosphide), CaS (calcium sulfide), Ca3N2 (calcium nitride), SiC (silicon carbide), etc.). In the presence of trace moisture, technical-grade calcium carbide emits an unpleasant odor reminiscent of garlic. Applications of calcium carbide include manufacture of acetylene gas, generation of acetylene in carbide lamps, manufacture of chemicals for fertilizer, and steelmaking. Production Calcium carbide is produced industrially in an electric arc furnace from a mixture of lime and coke at approximately . This is an endothermic reaction requiring per mole and high temperatures to drive off the carbon monoxide. ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Silver Acetylide
Silver acetylide is an inorganic chemical compound with the formula Ag2C2, a metal acetylide. The compound can be regarded as a salt of the weak acid, acetylene. The salt's anion consists of two carbon atoms linked by a triple bond. The alternate name "silver carbide" is rarely used, although the analogous calcium compound CaC2 is called calcium carbide. Silver acetylide is a high explosive. Synthesis Silver acetylide can be produced by passing acetylene gas through a solution of silver nitrate: :2 (aq) + (g) → (s) + 2 (aq) The reaction product is a greyish to white precipitate. This is the same synthesis from Berthelot in which he first found silver acetylide in 1866. The double salt is formed in acidic or neutral silver nitrate solutions. Performing the synthesis in basic ammonia solution does not allow the double salt to form, producing pure silver acetylide. To properly form the double salt, acetylene gas is passed through dilute silver nitrate and nitric acid solu ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organometallic Chemistry
Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide (metal carbonyls), cyanide, or carbide, are generally considered to be organometallic as well. Some related compounds such as transition metal hydrides and metal phosphine complexes are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term " metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, alkoxides, dialkylamides, and metal phosphine complexes are repres ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Transition Metals
In chemistry, a transition metal (or transition element) is a chemical element in the d-block of the periodic table (groups 3 to 12), though the elements of group 12 (and less often group 3) are sometimes excluded. They are the elements that can use d orbitals as valence orbitals to form chemical bonds. The lanthanide and actinide elements (the f-block) are called inner transition metals and are sometimes considered to be transition metals as well. Since they are metals, they are lustrous and have good electrical and thermal conductivity. Most (with the exception of group 11 and group 12) are hard and strong, and have high melting and boiling temperatures. They form compounds in any of two or more different oxidation states and bind to a variety of ligands to form coordination complexes that are often coloured. They form many useful alloys and are often employed as catalysts in elemental form or in compounds such as coordination complexes and oxides. Most are strongly paramagn ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organolithium Reagent
In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers. They have also been applied in asymmetric synthesis in the pharmaceutical industry. Due to the large difference in electronegativity between the carbon atom and the lithium atom, the C−Li bond is highly ionic. Owing to the polar nature of the C−Li bond, organolithium reagents are good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form. These reagents are highly reactive, and are sometimes pyrophoric. History and dev ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lithium Bis(trimethylsilyl)amide
Lithium bis(trimethylsilyl)amide is a lithiated organosilicon compound with the formula . It is commonly abbreviated as LiHMDS or Li(HMDS) (lithium hexamethyldisilazide - a reference to its conjugate acid HMDS) and is primarily used as a strong non-nucleophilic base and as a ligand. Like many lithium reagents, it has a tendency to aggregate and will form a cyclic trimer in the absence of coordinating species. Preparation LiHMDS is commercially available, but it can also be prepared by the deprotonation of bis(trimethylsilyl)amine with ''n''-butyllithium. This reaction can be performed ''in situ''. : Once formed, the compound can be purified by sublimation or distillation. Reactions and applications As a base LiHMDS is often used in organic chemistry as a strong non-nucleophilic base. Its conjugate acid has a p''K''a of ~26, making it is less basic than other lithium bases, such as LDA (p''K''a of conjugate acid ~36), but it is more sterically hindered and hence less nu ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lithium Amide
Lithium amide or lithium azanide is an inorganic compound with the chemical formula . It is a white solid with a tetragonal crystal structure. Lithium amide can be made by treating lithium metal with liquid ammonia: : Other lithium amides The conjugate bases of amines are known as amides. Thus, a ''lithium amide'' may also refer to any compound in the class of the lithium salt of an amine. These compounds have the general form , with the chemical lithium amide itself as the parent structure. Common lithium amides include lithium diisopropylamide (LDA), lithium tetramethylpiperidide (LiTMP), and lithium hexamethyldisilazide (LiHMDS). They are produced by the reaction of Li metal with the appropriate amine: : Lithium amides are very reactive compounds. Specifically, they are strong bases. Examples Lithium tetramethylpiperidide has been crystallised as a tetramer. On the other hand, the lithium derivative of bis(1-phenylethyl)amine crystallises as a trimer: It is also possibl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Liquid Ammonia
Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous waste, particularly among aquatic organisms, and it contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to 45% of the world's food and fertilizers. Around 70% of ammonia is used to make fertilisers in various forms and composition, such as urea and Diammonium phosphate. Ammonia in pure form is also applied directly into the soil. Ammonia, either directly or indirectly, is also a building block for the synthesis of many pharmaceutical products and is used in many commercial cleaning products. It is mainly collected by downward displacement of both air and water. Although common in nature—both terrestrially and in the outer planets of the Solar System—and in wide use, ammonia is both causti ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Superbase
A superbase is a compound that has a particularly high affinity for protons. Superbases are of theoretical interest and potentially valuable in organic synthesis. Superbases have been described and used since the 1850s.''Superbases for Organic Synthesis'' Ed. Ishikawa, T., John Wiley and Sons, Ltd.: West Sussex, UK. 2009. Definitions Generically IUPAC defines a superbase as a "compound having a very high basicity, such as lithium diisopropylamide." Superbases are often defined in two broad categories, organic and organometallic. Organic superbases are charge-neutral compounds with basicities greater than that of proton sponge (pKBH+ = 18.6 in MeCN)." In a related definition: any species with a higher absolute proton affinity (APA = 245.3 kcal/mol) and intrinsic gas phase basicity (GB = 239 kcal/mol) than proton sponge. Common superbases of this variety feature amidine, guanidine, and phosphazene functional groups. Strong superbases can be designed by utilizing multiple intram ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Superbase
A superbase is a compound that has a particularly high affinity for protons. Superbases are of theoretical interest and potentially valuable in organic synthesis. Superbases have been described and used since the 1850s.''Superbases for Organic Synthesis'' Ed. Ishikawa, T., John Wiley and Sons, Ltd.: West Sussex, UK. 2009. Definitions Generically IUPAC defines a superbase as a "compound having a very high basicity, such as lithium diisopropylamide." Superbases are often defined in two broad categories, organic and organometallic. Organic superbases are charge-neutral compounds with basicities greater than that of proton sponge (pKBH+ = 18.6 in MeCN)." In a related definition: any species with a higher absolute proton affinity (APA = 245.3 kcal/mol) and intrinsic gas phase basicity (GB = 239 kcal/mol) than proton sponge. Common superbases of this variety feature amidine, guanidine, and phosphazene functional groups. Strong superbases can be designed by utilizing multiple intram ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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