Organolithium
   HOME
*



picture info

Organolithium
In 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 so ..., organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) Chemical bond, 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 ionization, ionic. Owing to the polar nat ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Lithium
Lithium (from el, λίθος, lithos, lit=stone) is a chemical element with the symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard conditions, it is the least dense metal and the least dense solid element. Like all alkali metals, lithium is highly reactive and flammable, and must be stored in vacuum, inert atmosphere, or inert liquid such as purified kerosene or mineral oil. When cut, it exhibits a metallic luster, but moist air corrodes it quickly to a dull silvery gray, then black tarnish. It never occurs freely in nature, but only in (usually ionic) compounds, such as pegmatitic minerals, which were once the main source of lithium. Due to its solubility as an ion, it is present in ocean water and is commonly obtained from brines. Lithium metal is isolated electrolytically from a mixture of lithium chloride and potassium chloride. The nucleus of the lithium atom verges on instability, since the two stable lithium isotopes foun ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Metalation
Metalation (Alt. spelling: Metallation) is a chemical reaction that forms a bond to a metal. This reaction usually refers to the replacement of a halogen atom in an organic molecule with a metal atom, resulting in an organometallic compound. In the laboratory, metalation is commonly used to activate organic molecules during the formation of C—X bonds (where X is typically carbon, oxygen, or nitrogen), which are necessary for the synthesis of many organic molecules. In synthesis, metallated reagents are typically involved in nucleophilic substitution, single-electron-transfer (SET), and redox chemistry with functional groups on other molecules (including but not limited to ketones, aldehydes and alkyl halides). Metallated molecules may also participate in acid-base chemistry, with one organometallic reagent deprotonating an organic molecule to create a new organometallic reagent. The most common classes of metallated compounds are organolithium reagents and Grignard reagents. Ho ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  




Tert-Butyllithium
''tert''-Butyllithium is a chemical compound with the formula (CH3)3CLi. As an organolithium compound, it has applications in organic synthesis since it is a strong base, capable of deprotonating many carbon molecules, including benzene. ''tert''-Butyllithium is available commercially as hydrocarbon solutions; it is not usually prepared in the laboratory. Preparation ''tert''-Butyllithium is produced commercially by treating ''tert''-butyl chloride with lithium metal. Its synthesis was first reported by R. B. Woodward in 1941. Structure and bonding : Like other organolithium compounds, ''tert''-butyllithium is a cluster compound. Whereas ''n''-butyllithium exists both as a hexamer and a tetramer, ''tert''-butyllithium exists exclusively as a tetramer with a cubane structure. Bonding in organolithium clusters involves sigma delocalization and significant Li−Li bonding. Despite its complicated structure, ''tert''-butyllithium is usually depicted in equations as a mono ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Karl Ziegler
Karl Waldemar Ziegler (26 November 1898 – 12 August 1973) was a German chemist who won the Nobel Prize in Chemistry in 1963, with Giulio Natta, for work on polymers. The Nobel Committee recognized his "excellent work on organometallic compounds hich..led to new polymerization reactions and ... paved the way for new and highly useful industrial processes". He is also known for his work involving free-radicals, many-membered rings, and organometallic compounds, as well as the development of Ziegler–Natta catalyst. One of many awards Ziegler received was the Werner von Siemens Ring in 1960 jointly with Otto Bayer and Walter Reppe, for expanding the scientific knowledge of and the technical development of new synthetic materials. Biography Early life and education Karl Ziegler was born on 26 November 1898 in Helsa near Kassel, Germany and was the second son of Karl Ziegler, a Lutheran minister, and Luise Rall Ziegler. He attended Kassel-Bettenhausen in elementary school. An int ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Grignard Reaction
The Grignard reaction () is an organometallic chemical reaction in which alkyl, allyl, vinyl, or aryl-magnesium halides ( Grignard reagent) is added to a carbonyl group in an aldehyde or ketone. This reaction is important for the formation of carbon–carbon bonds. The reaction of an organic halide with magnesium is ''not'' a Grignard reaction, but provides a Grignard reagent. : Grignard reactions and reagents were discovered by and are named after the French chemist François Auguste Victor Grignard (University of Nancy, France), who published it in 1900 and was awarded the 1912 Nobel Prize in Chemistry for this work. Reaction mechanism Because carbon is more electronegative than magnesium, the carbon attached to magnesium functions as a nucleophile and attacks the electrophilic carbon atom that is present within the polar bond of a carbonyl group. The addition of the Grignard reagent to the carbonyl typically proceeds through a six-membered ring transition state. Based on ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Anionic Polymerization
In polymer chemistry, anionic addition polymerization is a form of chain-growth polymerization or addition polymerization that involves the polymerization of monomers initiated with anions. The type of reaction has many manifestations, but traditionally vinyl monomers are used.Hsieh, H.;Quirk, R. ''Anionic Polymerization: Principles and practical applications''; Marcel Dekker, Inc.: New York, 1996.Quirk, R. Anionic Polymerization. In ''Encyclopedia of Polymer Science and Technology''; John Wiley and Sons: New York, 2003. Often anionic polymerization involves living polymerizations, which allows control of structure and composition. History As early as 1936, Karl Ziegler proposed that anionic polymerization of styrene and butadiene by consecutive addition of monomer to an alkyl lithium initiator occurred without chain transfer or termination. Twenty years later, living polymerization was demonstrated by Michael Szwarc and coworkers. In one of the breakthrough events in the fiel ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


Methyllithium
Methyllithium is the simplest organolithium reagent with the empirical formula CH3Li. This s-block organometallic compound adopts an oligomeric structure both in solution and in the solid state. This highly reactive compound, invariably used in solution with an ether as the solvent, is a reagent in organic synthesis as well as organometallic chemistry. Operations involving methyllithium require anhydrous conditions, because the compound is highly reactive toward water. Oxygen and carbon dioxide are also incompatible with MeLi. Methyllithium is usually not prepared, but purchased as a solution in various ethers. Synthesis In the direct synthesis, methyl bromide is treated with a suspension of lithium in diethyl ether. :2 Li + MeBr → LiMe + LiBr The lithium bromide forms a complex with the methyllithium. Most commercially available methyllithium consists of this complex. "Halide-free" methyllithium is prepared from methyl chloride. Lithium chloride precipitates from the diethyl ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Building Block Of Alkyllithium Aggregates
A building, or edifice, is an enclosed structure with a roof and walls standing more or less permanently in one place, such as a house or factory (although there's also portable buildings). Buildings come in a variety of sizes, shapes, and functions, and have been adapted throughout history for a wide number of factors, from building materials available, to weather conditions, land prices, ground conditions, specific uses, prestige, and aesthetic reasons. To better understand the term ''building'' compare the list of nonbuilding structures. Buildings serve several societal needs – primarily as shelter from weather, security, living space, privacy, to store belongings, and to comfortably live and work. A building as a shelter represents a physical division of the human habitat (a place of comfort and safety) and the ''outside'' (a place that at times may be harsh and harmful). Ever since the first cave paintings, buildings have also become objects or canvasses of much artistic ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Covalent
A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atoms, when they share electrons, is known as covalent bonding. For many molecules, the sharing of electrons allows each atom to attain the equivalent of a full valence shell, corresponding to a stable electronic configuration. In organic chemistry, covalent bonding is much more common than ionic bonding. Covalent bonding also includes many kinds of interactions, including σ-bonding, π-bonding, metal-to-metal bonding, agostic interactions, bent bonds, three-center two-electron bonds and three-center four-electron bonds. The term ''covalent bond'' dates from 1939. The prefix ''co-'' means ''jointly, associated in action, partnered to a lesser degree, '' etc.; thus a "co-valent bond", in essence, means that the atoms share " valence", such a ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Electrostatic
Electrostatics is a branch of physics that studies electric charges at rest (static electricity). Since classical times, it has been known that some materials, such as amber, attract lightweight particles after rubbing. The Greek word for amber, (), was thus the source of the word 'electricity'. Electrostatic phenomena arise from the forces that electric charges exert on each other. Such forces are described by Coulomb's law. Even though electrostatically induced forces seem to be rather weak, some electrostatic forces are relatively large. The force between an electron and a proton, which together make up a hydrogen atom, is about 36 orders of magnitude stronger than the gravitational force acting between them. There are many examples of electrostatic phenomena, from those as simple as the attraction of plastic wrap to one's hand after it is removed from a package, to the apparently spontaneous explosion of grain silos, the damage of electronic components during manufacturi ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Computational Chemistry
Computational chemistry is a branch of chemistry that uses computer simulation to assist in solving chemical problems. It uses methods of theoretical chemistry, incorporated into computer programs, to calculate the structures and properties of molecules, groups of molecules, and solids. It is essential because, apart from relatively recent results concerning the hydrogen molecular ion (dihydrogen cation, see references therein for more details), the quantum many-body problem cannot be solved analytically, much less in closed form. While computational results normally complement the information obtained by chemical experiments, it can in some cases predict hitherto unobserved chemical phenomena. It is widely used in the design of new drugs and materials. Examples of such properties are structure (i.e., the expected positions of the constituent atoms), absolute and relative (interaction) energies, electronic charge density distributions, dipoles and higher multipole moments, vi ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]