Kinetic Resolution
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Kinetic Resolution
In organic chemistry, kinetic resolution is a means of differentiating two enantiomers in a racemic mixture. In kinetic resolution, two enantiomers react with different reaction rates in a chemical reaction with a chiral catalyst or reagent, resulting in an enantioenriched sample of the less reactive enantiomer. As opposed to chiral resolution, kinetic resolution does not rely on different physical properties of diastereomeric products, but rather on the different chemical properties of the racemic starting materials. The enantiomeric excess (ee) of the unreacted starting material continually rises as more product is formed, reaching 100% just before full completion of the reaction. Kinetic resolution relies upon differences in reactivity between enantiomers or enantiomeric complexes. Kinetic resolution can be used for the preparation of chiral molecules in organic synthesis. Kinetic resolution reactions utilizing purely synthetic reagents and catalysts are much less common tha ...
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Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical ( in silico) study. The range of chemicals studied in organic chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but also containing other elements, especially oxygen, nitrogen, sulfur, phosphorus (i ...
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Willy Marckwald
Willy Marckwald (1864, Jakobskirch, Germany – 1942, Rolândia, Brazil) was a German chemist. He was nominated for the Nobel Prize in Chemistry in 1922 by Gustav Tammann and again in 1929 by Niels Bohr, Dirk Coster and George de Hevesy. Biography Marckwald studied at Berlin's Friedrich-Wilhelms-Universität and received there from the First Chemical Institute in 1886 his Promotierung under A. W. Hofmann with a dissertation on organic chemistry entitled ''Beitrag zur Kenntniss der Thialdehyde und Thialdine''. By his research on furans, Marckwald received his Habilitation in a very short time in 1889 under the supervision of A. W. Hofmann at Friedrich-Wilhelms-Universität Berlin. In 1899 Marckwald became one of the department heads at the Second Chemical Institute. He held this Privatdozent-level position until his age-related retirement in 1930. From 1928 to 1931 he was the board chair of the German Chemical Society. In 1890 Marckwald married Margarete Salomon (1871–1908 ...
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Chiral Pool Synthesis
The chiral pool is a "collection of abundant enantiopure building blocks provided by nature" used in synthesis. In other words, a chiral pool would be a large quantity of common organic enantiomers. Contributors to the chiral pool are amino acids, sugars, and terpenes. Their use improves the efficiency of total synthesis. Not only does the chiral pool contribute a premade carbon skeleton, their chirality is usually preserved in the remainder of the reaction sequence. This strategy is especially helpful if the desired molecule resembles cheap enantiopure natural products. Many times, suitable enantiopure starting materials cannot be identified. The alternative to the use of the chiral pool is asymmetric synthesis, whereby achiral precursors are employed or racemic intermediates are resolved. Examples The use of the chiral pool is illustrated by the synthesis of the anticancer drug paclitaxel (Taxol). The incorporation of the C10 precursor verbenone, a member of the chiral pool, ...
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Enantioselective Synthesis
Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts." Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer. Enantiomers are stereoisomers that have opposite configurations at every chiral center. Diastereomers are stereoisomers that differ at one or more chiral centers. Enantioselective synthesis is a key process in modern chemistry and is particularly important in the field of pharmaceuticals, as the different enantiomers or diastereomers of a molecule often have different biological activity. Overview Many of the building blocks of biological systems such as sugars and amino acids are produced exclusively a ...
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Parameter
A parameter (), generally, is any characteristic that can help in defining or classifying a particular system (meaning an event, project, object, situation, etc.). That is, a parameter is an element of a system that is useful, or critical, when identifying the system, or when evaluating its performance, status, condition, etc. ''Parameter'' has more specific meanings within various disciplines, including mathematics, computer programming, engineering, statistics, logic, linguistics, and electronic musical composition. In addition to its technical uses, there are also extended uses, especially in non-scientific contexts, where it is used to mean defining characteristics or boundaries, as in the phrases 'test parameters' or 'game play parameters'. Modelization When a system is modeled by equations, the values that describe the system are called ''parameters''. For example, in mechanics, the masses, the dimensions and shapes (for solid bodies), the densities and the visco ...
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Racemate
In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. History The first known racemic mixture was racemic acid, which Louis Pasteur found to be a mixture of the two enantiomeric isomers of tartaric acid. He manually separated the crystals of a mixture by hand, starting from an aqueous solution of the sodium ammonium salt of racemate tartaric acid. Pasteur benefited from the fact that ammonium tartrate salt that gives enantiomeric crystals with distinct crystal forms (at 77 °F). Reasoning from the macroscopic scale down to the molecular, he reckoned that the molecules had to have non-superimposable mirror images. A sample with only a single enantiomer is an ''enantiomerically pure'' or ''enantiopure'' compound. Etymology From racemic acid found in grapes; from Latin ''racemus'', me ...
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Reaction Rate Constant
In chemical kinetics a reaction rate constant or reaction rate coefficient, ''k'', quantifies the rate and direction of a chemical reaction. For a reaction between reactants A and B to form product C the reaction rate is often found to have the form: r = k(T) mathrmm mathrm Here ''k''(''T'') is the reaction rate constant that depends on temperature, and and are the molar concentrations of substances A and B in moles per unit volume of solution, assuming the reaction is taking place throughout the volume of the solution. (For a reaction taking place at a boundary, one would use moles of A or B per unit area instead.) The exponents ''m'' and ''n'' are called partial orders of reaction and are ''not'' generally equal to the stoichiometric coefficients ''a'' and ''b''. Instead they depend on the reaction mechanism and can be determined experimentally. Elementary steps For an elementary step, there ''is'' a relationship between stoichiometry and rate law, as determined by ...
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Kinetic Resolution Free Energy Diagram
Kinetic (Ancient Greek: κίνησις “kinesis”, movement or to move) may refer to: * Kinetic theory, describing a gas as particles in random motion * Kinetic energy, the energy of an object that it possesses due to its motion Art and entertainment * Kinetic art, a form of art involving mechanical and/or random movement, including optical illusions. * ''Kinetic'', the 13th episode of the first season of the TV series ''Smallville'' * ''Kinetic'' (comics), a comic by Allan Heinberg and Kelley Pucklett * "Kinetic" (song), a song by Radiohead Companies * Kinetic Engineering Limited, Indian automotive manufacturer * Kinetic Group, Australian-based public transport company Technology * "Kinetic", Seiko's trademark for its automatic quartz technology * The ''Kinetic camera system'' by Birt Acres (1854–1918), photographer and film pioneer * Kinetic projectile Military terminology * Kinetic military action See also * * * Kinetics (other) * Dynamics (disambigua ...
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Gibbs Free Energy
In thermodynamics, the Gibbs free energy (or Gibbs energy; symbol G) is a thermodynamic potential that can be used to calculate the maximum amount of work that may be performed by a thermodynamically closed system at constant temperature and pressure. It also provides a necessary condition for processes such as chemical reactions that may occur under these conditions. The Gibbs free energy change , measured in joules in SI) is the ''maximum'' amount of non-expansion work that can be extracted from a closed system (one that can exchange heat and work with its surroundings, but not matter) at fixed temperature and pressure. This maximum can be attained only in a completely reversible process. When a system transforms reversibly from an initial state to a final state under these conditions, the decrease in Gibbs free energy equals the work done by the system to its surroundings, minus the work of the pressure forces. The Gibbs energy is the thermodynamic potential that is m ...
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Kinetic Resolution Of Mandelic Acid With (-)-menthol
Kinetic (Ancient Greek: κίνησις “kinesis”, movement or to move) may refer to: * Kinetic theory, describing a gas as particles in random motion * Kinetic energy, the energy of an object that it possesses due to its motion Art and entertainment * Kinetic art, a form of art involving mechanical and/or random movement, including optical illusions. * ''Kinetic'', the 13th episode of the first season of the TV series ''Smallville'' * ''Kinetic'' (comics), a comic by Allan Heinberg and Kelley Pucklett * "Kinetic" (song), a song by Radiohead Companies * Kinetic Engineering Limited, Indian automotive manufacturer * Kinetic Group, Australian-based public transport company Technology * "Kinetic", Seiko's trademark for its automatic quartz technology * The ''Kinetic camera system'' by Birt Acres (1854–1918), photographer and film pioneer * Kinetic projectile Military terminology * Kinetic military action See also * * * Kinetics (other) * Dynamics (disambigua ...
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Menthol
Menthol is an organic compound, more specifically a monoterpenoid, made synthetically or obtained from the oils of corn mint, peppermint, or other mints. It is a waxy, clear or white crystalline substance, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (−)-menthol, which is assigned the (1''R'',2''S'',5''R'') configuration. Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation. Menthol also acts as a weak κ-opioid receptor agonist. Structure Natural menthol exists as one pure stereoisomer, nearly always the (1''R'',2''S'',5''R'') form (bottom left corner of the diagram below). The eight possible stereoisomers are: : In the natural compound, the isopropyl group is in the '' trans'' orientation to both the methyl and hydroxyl groups. Thus, it can be drawn in any of the ways shown: : The (+)- and (−)- enantiomers of menthol are the most stab ...
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Mandelic Acid
Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C6H5CH(OH)CO2H. It is a white crystalline solid that is soluble in water and polar organic solvents. It is a useful precursor to various drugs. The molecule is chiral. The racemic mixture is known as ''paramandelic acid''. Isolation, synthesis, occurrence Mandelic acid was discovered in 1831 by the German pharmacist Ferdinand Ludwig Winckler (1801–1868) while heating amygdalin, an extract of bitter almonds, with diluted hydrochloric acid. The name is derived from the German "Mandel" for "almond". Mandelic acid is usually prepared by the acid-catalysed hydrolysis of mandelonitrile, which is the cyanohydrin of benzaldehyde. Mandelonitrile can also be prepared by reacting benzaldehyde with sodium bisulfite to give the corresponding adduct, forming mandelonitrile with sodium cyanide, which is hydrolyzed: : Alternatively, it can be prepared by base hydrolysis of phenylchloroacetic acid as well as dibroma ...
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