Whitmore 1,2 Shift
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Whitmore 1,2 Shift
A 1,2-rearrangement or 1,2-migration or 1,2-shift or Whitmore 1,2-shift is an organic reaction where a substituent moves from one atom to another atom in a chemical compound. In a 1,2 shift the movement involves two adjacent atoms but moves over larger distances are possible. In the example below the substituent R moves from carbon atom C2 to C3. The rearrangement is intramolecular and the starting compound and reaction product are structural isomers. The 1,2-rearrangement belongs to a broad class of chemical reactions called rearrangement reactions. A rearrangement involving a hydrogen atom is called a 1,2-hydride shift. If the substituent being rearranged is an alkyl group, it is named according to the alkyl group's anion: i.e. 1,2-methanide shift, 1,2-ethanide shift, etc. Reaction mechanism A 1,2-rearrangement is often initialised by the formation of a reactive intermediate such as: *a carbocation by heterolysis in a nucleophilic rearrangement or anionotropic rear ...
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Frank C
Frank or Franks may refer to: People * Frank (given name) * Frank (surname) * Franks (surname) * Franks, a medieval Germanic people * Frank, a term in the Muslim world for all western Europeans, particularly during the Crusades - see Farang Currency * Liechtenstein franc or frank, the currency of Liechtenstein since 1920 * Swiss franc or frank, the currency of Switzerland since 1850 * Westphalian frank, currency of the Kingdom of Westphalia between 1808 and 1813 * The currencies of the German-speaking cantons of Switzerland (1803–1814): ** Appenzell frank ** Argovia frank ** Basel frank ** Berne frank ** Fribourg frank ** Glarus frank ** Graubünden frank ** Luzern frank ** Schaffhausen frank ** Schwyz frank ** Solothurn frank ** St. Gallen frank ** Thurgau frank ** Unterwalden frank ** Uri frank ** Zürich frank Places * Frank, Alberta, Canada, an urban community, formerly a village * Franks, Illinois, United States, an unincorporated community * Franks, Missouri, United ...
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Homolysis (chemistry)
In chemistry, homolysis () or homolytic fission is the dissociation of a molecular bond by a process where each of the fragments (an atom or molecule) retains one of the originally bonded electrons. During homolytic fission of a neutral molecule with an even number of electrons, two free radicals will be generated. That is, the two electrons involved in the original bond are distributed between the two fragment species. Bond cleavage is also possible by a process called heterolysis. The energy involved in this process is called bond dissociation energy (BDE). BDE is defined as the "enthalpy (per mole) required to break a given bond of some specific molecular entity by homolysis," symbolized as ''D''. BDE is dependent on the strength of the bond, which is determined by factors relating to the stability of the resulting radical species. Because of the relatively high energy required to break bonds in this manner, homolysis occurs primarily under certain circumstances: * Light ...
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Mole (unit)
The mole, symbol mol, is the unit of amount of substance in the International System of Units (SI). The quantity amount of substance is a measure of how many elementary entities of a given substance are in an object or sample. The mole is defined as containing exactly elementary entities. Depending on what the substance is, an elementary entity may be an atom, a molecule, an ion, an ion pair, or a subatomic particle such as an electron. For example, 10 moles of water (a chemical compound) and 10 moles of mercury (a chemical element), contain equal amounts of substance and the mercury contains exactly one atom for each molecule of the water, despite the two having different volumes and different masses. The number of elementary entities in one mole is known as the Avogadro number, which is the approximate number of nucleons (protons or neutrons) in one gram of ordinary matter. The previous definition of a mole was simply the number of elementary entities equal to that of 12 gram ...
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Calorie
The calorie is a unit of energy. For historical reasons, two main definitions of "calorie" are in wide use. The large calorie, food calorie, or kilogram calorie was originally defined as the amount of heat needed to raise the temperature of one kilogram of water by one degree Celsius (or one kelvin). The small calorie or gram calorie was defined as the amount of heat needed to cause the same increase in one gram of water. Thus, 1 large calorie is equal to 1000 small calories. In nutrition and food science, the term ''calorie'' and the symbol ''cal'' almost always refers to the large unit. It is generally used in publications and package labels to express the energy value of foods in per serving or per weight, recommended dietary caloric intake, metabolic rates, etc. Some authors recommend the spelling ''Calorie'' and the symbol ''Cal'' (both with a capital C) to avoid confusion; however, this convention is often ignored. In physics and chemistry the word ''calorie'' and i ...
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Aryl Radical
An aryl radical in organic chemistry is a reactive intermediate and an arene compound incorporating one free radical carbon atom as part of the ring structure. As such it is the radical counterpart of the arenium ion. The parent compound is the phenyl radical .''Minireview Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts'' Markus R. Heinrich Chemistry - A European Journal 2008 volume 15 issue 4, pages 820 - 833 Aryl radicals are intermediates in certain organic reactions. Synthesis Aryl radicals can be obtained via aryl diazonium salts. Alternatives for these salts are certain aryl triazenes and aryl hydrazines. Aryl bromides and iodides can be converted to aryl radicals via tributyltin hydride and related compounds and silyl hydrides. Aryl halides can also be converted via electrochemical cathodic reduction The mushroom ''Stephanospora caroticolor'' is suspected to generate an aryl radical as part of its biological chemical defe ...
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Electron Spin Resonance
Electron paramagnetic resonance (EPR) or electron spin resonance (ESR) spectroscopy is a method for studying materials that have unpaired electrons. The basic concepts of EPR are analogous to those of nuclear magnetic resonance (NMR), but the spins excited are those of the electrons instead of the atomic nuclei. EPR spectroscopy is particularly useful for studying metal complexes and organic radicals. EPR was first observed in Kazan State University by Soviet physicist Yevgeny Zavoisky in 1944, and was developed independently at the same time by Brebis Bleaney at the University of Oxford. Theory Origin of an EPR signal Every electron has a magnetic moment and spin quantum number s = \tfrac , with magnetic components m_\mathrm = + \tfrac or m_\mathrm = - \tfrac . In the presence of an external magnetic field with strength B_\mathrm , the electron's magnetic moment aligns itself either antiparallel ( m_\mathrm = - \tfrac ) or parallel ( m_\mathrm = + \tfrac ) to the fi ...
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Chem
Chem may refer to: * Chemistry practical waali mam *Chemistry *Chemical * ''Chem'' (journal), a scientific journal published by Cell Press *Post apocalyptic slang for "drugs", medicinal or otherwise in the Fallout video game series. In Ancient Egyptian usage: * ''Khem'' (also spelt ''Chem''), the Egyptian word for "black" * Min (god), in the past erroneously named ''Khem'' CHEM may refer to : *A metabolic panel: for instance, CHEM-7, which is the basic metabolic panel *CHEM-DT CHEM-DT is the TVA owned-and-operated television station in Trois-Rivières, Quebec, Canada. It broadcasts a high-definition digital signal on VHF channel 8 from a transmitter on Rue Principale in Notre-Dame-du-Mont-Carmel. Owned by the Grou ..., a Canadian television channel See also * Chemo (other) * Kemi, a place in Finland {{disambig ...
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Heinrich Otto Wieland
Heinrich Otto Wieland (; 4 June 1877 – 5 August 1957) was a German chemist. He won the 1927 Nobel Prize in Chemistry for his research into the bile acids. Career In 1901 Wieland received his doctorate at the University of Munich while studying under Johannes Thiele. In 1904 he completed his habilitation, then continued to teach at the university and starting in 1907 was a consultant for Boehringer Ingelheim. In 1914 he became associate professor for special topics in organic chemistry, and director of the Organic Division of the State Laboratory in Munich. From 1917 to 1918 Wieland worked in the service of the (KWI) Kaiser Wilhelm Institute for Physical Chemistry and Electrochemistry in Dahlem then led by Fritz Haber as an alternative to regular military service. There he was involved in weapons research for instance finding new synthetic routes for mustard gas. He is also credited with the first synthesis of Adamsite. From 1913 to 1921, he was Professor at the Technica ...
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Benzilic Acid Rearrangement
The benzilic acid rearrangement is formally the 1,2-rearrangement of 1,2-diketones to form α- hydroxy–carboxylic acids using a base. This reaction receives its name from the reaction of benzil with potassium hydroxide to form benzilic acid. First performed by Justus von Liebig in 1838, it is the first reported example of a rearrangement reaction.Nerve Agent Precursors: Benzilic acid and Methyl Benzilate
, Factsheets on Chemical and Biological Warfare Agents, Chemical precursors.
It has become a classic reaction in organic synthesis and has been reviewed many times before. It can be viewed as an intramolecular

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Wagner–Meerwein Rearrangement
A Wagner–Meerwein rearrangement is a class of carbocation 1,2-rearrangement reactions in which a hydrogen, alkyl or aryl group migrates from one carbon to a neighboring carbon. They can be described as cationic ,2sigmatropic rearrangements, proceeding suprafacially and with stereochemical retention. As such, a Wagner–Meerwein shift is a thermally allowed pericyclic process with the Woodward-Hoffmann symbol ω0s_+_σ2s.html" ;"title="sub>ω0s + σ2s">sub>ω0s + σ2s They are usually facile, and in many cases, they can take place at temperatures as low as –120 °C. The reaction is named after the Russian chemist Yegor Yegorovich Vagner; he had German origin and published in German journals as Georg Wagner; and Hans Meerwein. Several reviews have been published. The rearrangement was first discovered in bicyclic terpenes for example the conversion of isoborneol to camphene: The story of the rearrangement reveals that many scientists were puzzled with this and relate ...
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Transition State
In chemistry, the transition state of a chemical reaction is a particular configuration along the reaction coordinate. It is defined as the state corresponding to the highest potential energy along this reaction coordinate. It is often marked with the double dagger ‡ symbol. As an example, the transition state shown below occurs during the SN2 reaction of bromoethane with a hydroxide anion: The activated complex of a reaction can refer to either the transition state or to other states along the reaction coordinate between reactants and products, especially those close to the transition state.Peter Atkins and Julio de Paula, ''Physical Chemistry'' (8th ed., W.H. Freeman 2006), p.809 According to the transition state theory, once the reactants have passed through the transition state configuration, they always continue to form products. History of concept The concept of a transition state has been important in many theories of the rates at which chemical reactions occ ...
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