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Zincke Reaction
The Zincke reaction is an organic reaction, named after Theodor Zincke, in which a pyridine is transformed into a pyridinium salt by reaction with 2,4-dinitro-chlorobenzene and a primary amine. The Zincke reaction should not be confused with the Zincke-Suhl reaction or the Zincke nitration. Furthermore, the Zincke reaction has nothing to do with the chemical element zinc. Reaction mechanism The first reaction is the formation of the ''N''-2,4-dinitrophenyl-pyridinium salt (2). This salt is typically isolated and purified by recrystallization. Upon heating a primary amine with the ''N''-2,4-dinitrophenyl-pyridinium salt (2), the addition of the amine leads to the opening of the pyridinium ring. A second addition of amine leads to the displacement of 2,4-dinitroaniline (5) and formation of the König salt (6a and 6b). The trans-cis-trans isomer of the König salt (6a) can react by either sigmatropic rearrangement or nucleophilic addition of a zwitterionic intermediate to ...
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Theodor Zincke
Ernst Carl Theodor Zincke (19 May 1843 – 17 March 1928) was a German chemist and the academic adviser of Otto Hahn. Life Theodor Zincke was born in Uelzen on 19 May 1843. He became a pharmacist and graduated in Göttingen with his Staatsexamen. He began studying chemistry with Friedrich Wöhler and received his Ph.D in 1869. He joined the group of August Kekulé at the University of Bonn, and in 1875 became professor at the University of Marburg where he remained until his retirement in 1913. He developed Zincke reaction, Zincke–Suhl reaction in 1906 (together with R. Suhl) and in 1900 Zincke nitration. Theodor Zincke died on 17 March 1928 in Marburg Marburg ( or ) is a university town in the German federal state (''Bundesland'') of Hesse, capital of the Marburg-Biedenkopf district (''Landkreis''). The town area spreads along the valley of the river Lahn and has a population of approxima .... References * * {{DEFAULTSORT:Zincke, Theodor 1843 births 1928 dea ...
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Zwitterion
In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively- and negatively-charged functional groups. : With amino acids, for example, in solution a chemical equilibrium will be established between the "parent" molecule and the zwitterion. Betaines are zwitterions that cannot isomerize to an all-neutral form, such as when the positive charge is located on a quaternary ammonium group. Similarly, a molecule containing a phosphonium group and a carboxylate group cannot isomerize. Amino acids The equilibrium is established in two stages. In the first stage, a proton is transferred from the carboxyl group to a water molecule: :H2N(R)CO2H + H2O H2N(R)CO2- + H3O+ In the second stage, a proton is transferred from the hydronium ion to the amine group: :H2N(R)CO2- + H3O+ H3N+ (R)CO2- + H2O Overall, the reaction is an isomerization reaction :H2N(R)CO2H H3N+ (R)CO2- The ratio of the concentrations of the two spec ...
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Isoquinoline
Isoquinoline is a heterocyclic aromatic organic compound. It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. In a broader sense, the term isoquinoline is used to make reference to isoquinoline derivatives. 1-Benzylisoquinoline is the structural backbone in naturally occurring alkaloids including papaverine. The isoquinoline ring in these natural compound derives from the aromatic amino acid tyrosine. Properties Isoquinoline is a colorless hygroscopic liquid at temperatures above its melting point with a penetrating, unpleasant odor. Impure samples can appear brownish, as is typical for nitrogen heterocycles. It crystallizes in platelets that have a low solubility in water but dissolve well in ethanol, acetone, diethyl ether, carbon disulfide, and other common organic solvents. It is also soluble in dilute acids as the protonated derivative. Being an analog of pyridine, isoquinolin ...
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Chirality (chemistry)
In chemistry, a molecule or ion is called chiral () if it cannot be superposed on its mirror image by any combination of rotation (geometry), rotations, translation (geometry), translations, and some Conformational isomerism, conformational changes. This geometric property is called chirality (). The terms are derived from Ancient Greek χείρ (''cheir'') 'hand'; which is the canonical example of an object with this property. A chiral molecule or ion exists in two stereoisomers that are mirror images of each other, called enantiomers; they are often distinguished as either "right-handed" or "left-handed" by their absolute configuration or some other criterion. The two enantiomers have the same chemical properties, except when reacting with other chiral compounds. They also have the same physics, physical properties, except that they often have opposite optical activity, optical activities. A homogeneous mixture of the two enantiomers in equal parts is said to be racemic mixtu ...
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Wang Resin
Wang may refer to: Names * Wang (surname) (王), a common Chinese surname * Wāng (汪), a less common Chinese surname * Titles in Chinese nobility * A title in Korean nobility * A title in Mongolian nobility Places * Wang River in Thailand * Wang Township, Minnesota, a township in the United States * Wang, Bavaria, a town in the district of Freising, Bavaria, Germany * Wang, Austria, a town in the district of Scheibbs in Lower Austria * An abbreviation for the town of Wangaratta, Australia * Wang Theatre, in Boston, Massacheussetts * Charles B. Wang Center, an Asian American center at Stony Brook University Other * Wang (Tibetan Buddhism), a form of empowerment or initiation * Wang tile, in mathematics, are a class of formal systems * Wang (musical), ''Wang'' (musical), an 1891 New York musical * Wang Film Productions, Taiwanese-American animation studios * Wang Laboratories, an American computer company founded by Dr. An Wang * WWNG, a radio station (1330 AM) licensed to ...
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Solid-phase Synthesis
In chemistry, solid-phase synthesis is a method in which molecules are covalently bound on a solid support material and synthesised step-by-step in a single reaction vessel utilising selective protecting group chemistry. Benefits compared with normal synthesis in a liquid state include: * High efficiency and throughput * Increased simplicity and speed The reaction can be driven to completion and high yields through the use of excess reagent. In this method, building blocks are protected at all reactive functional groups. The order of functional group reactions can be controlled by the order of deprotection. This method is used for the synthesis of peptides, deoxyribonucleic acid ( DNA), ribonucleic acid (RNA), and other molecules that need to be synthesised in a certain alignment. More recently, this method has also been used in combinatorial chemistry and other synthetic applications. The process was originally developed in the 1950s and 1960s by Robert Bruce Merrifield in orde ...
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Ring-closing Reaction
A cyclic compound (or ring compound) is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon (i.e., are carbocycles), none of the atoms are carbon (inorganic cyclic compounds), or where both carbon and non-carbon atoms are present (heterocyclic compounds). Depending on the ring size, the bond order of the individual links between ring atoms, and their arrangements within the rings, carbocyclic and heterocyclic compounds may be aromatic or non-aromatic; in the latter case, they may vary from being fully saturated to having varying numbers of multiple bonds between the ring atoms. Because of the tremendous diversity allowed, in combination, by the valences of common atoms and their ability to form rings, the number of possible cyclic structures, even of small size (e.g., < 17 total atoms) numbers in the many b ...
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Ring-opening Reaction
A cyclic compound (or ring compound) is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon (i.e., are carbocycles), none of the atoms are carbon (inorganic cyclic compounds), or where both carbon and non-carbon atoms are present (heterocyclic compounds). Depending on the ring size, the bond order of the individual links between ring atoms, and their arrangements within the rings, carbocyclic and heterocyclic compounds may be aromatic or non-aromatic; in the latter case, they may vary from being fully saturated to having varying numbers of multiple bonds between the ring atoms. Because of the tremendous diversity allowed, in combination, by the valences of common atoms and their ability to form rings, the number of possible cyclic structures, even of small size (e.g., < 17 total atoms) numbers in the many ...
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ANRORC Mechanism
The ANRORC mechanism in organic chemistry describes a special type of substitution reaction. ANRORC stands for Addition of the Nucleophile, Ring Opening, and Ring Closure in nucleophilic attack on ring systems and it helps to explain product formation and distribution in some nucleophilic substitutions especially in heterocyclic compounds. It is widely used in medicinal chemistry. This reaction mechanism has been extensively studied in reactions of metal amide nucleophiles (such as sodium amide) and substituted pyrimidines (for instance 4-phenyl-6-bromopyrimidine 1) in ammonia at low temperatures. The main reaction product is 4-phenyl-6-aminopyrimidine 2 with the bromine substituent replaced by an amine. This rules out the formation of an aryne intermediate A which would also give the 5-substituted isomer. The exclusion of a second intermediate in this reaction, the Meisenheimer complex B in favor of the ring-opened ANRORC intermediate is based on several pieces of evidence. Wi ...
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Zincke Reaction Mechanism2
Zincke is a surname. Notable people with the surname include: * Christian Friedrich Zincke, German painter * Foster Barham Zincke (1817–1893), clergyman, traveler, and antiquary * Georg Heinrich Zincke, German jurist and cameralist * Theodor Zincke Ernst Carl Theodor Zincke (19 May 1843 – 17 March 1928) was a German chemist and the academic adviser of Otto Hahn. Life Theodor Zincke was born in Uelzen on 19 May 1843. He became a pharmacist and graduated in Göttingen with his Staatsexame ..., German chemist See also * Zinke {{Surname ...
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