Cyclooctatetraene
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Cyclooctatetraene
1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane, with the formula C8H8. It is also known as nnulene. This polyunsaturated hydrocarbon is a colorless to light yellow flammable liquid at room temperature. Because of its stoichiometric relationship to benzene, COT has been the subject of much research and some controversy. Unlike benzene, C6H6, cyclooctatetraene, C8H8, is not aromatic, although its dianion, ( cyclooctatetraenide), is. Its reactivity is characteristic of an ordinary polyene, i.e. it undergoes addition reactions. Benzene, by contrast, characteristically undergoes substitution reactions, not additions. History 1,3,5,7-Cyclooctatetraene was initially synthesized by Richard Willstätter in Munich in 1905 using pseudopelletierine as the starting material and the Hofmann elimination as the key transformation: : Willstätter noted that the compound did not exhibit the expected aromaticity. Between 1939 and 1943, chemists throug ...
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Walter Reppe
Walter Julius Reppe (29 July 1892 in Göringen – 26 July 1969 in Heidelberg) was a German chemist. He is notable for his contributions to the chemistry of acetylene. Education and career Walter Reppe began his study of the natural sciences University of Jena in 1911. Interrupted by the First World War, he obtained his doctorate in Munich in 1920. In 1921, Reppe worked for BASF's main laboratory. From 1923, he worked on the catalytic dehydration of formamide to prussic acid in the indigo laboratory, developing this procedure for industrial use. In 1924, he left research for 10 years, only resuming it in 1934. Acetylene chemistry Reppe began his interest in acetylene in 1928. Acetylene is a gas which can take part in many chemical reactions. However, it is explosive and accidents often occurred. Because of this danger, small quantities of acetylene were used at a time, and always without high pressures. In fact, it was forbidden to compress acetylene over 1.5 bar at BASF. To ...
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Jahn–Teller Effect
The Jahn–Teller effect (JT effect or JTE) is an important mechanism of spontaneous symmetry breaking in molecular and solid-state systems which has far-reaching consequences in different fields, and is responsible for a variety of phenomena in spectroscopy, stereochemistry, crystal chemistry, molecular and solid-state physics, and materials science. The effect is named for Hermann Arthur Jahn and Edward Teller, who first reported studies about it in 1937.Bunker, Philip R.; Jensen, Per (1998) ''Molecular Symmetry and Spectroscopy'' (2nd ed.). NRC Research Press, Ottaw/ref> Simplified overview The Jahn–Teller effect, sometimes also referred to as Jahn–Teller distortion, describes the geometrical distortion of molecules and ions that result from certain electron configurations. The Jahn–Teller theorem essentially states that any non-linear molecule with a spatially degenerate electronic ground state will undergo a geometrical distortion that removes that degeneracy, because t ...
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Cyclooctatetraenide Anion
In chemistry, the cyclooctatetraenide anion or cyclooctatetraenide, more precisely cyclooctatetraenediide, is an aromatic species with a formula of 8H8sup>2− and abbreviated as COT2−. It is the dianion of cyclooctatetraene. Salts of the cyclooctatetraenide anion can be stable, e.g., Dipotassium cyclooctatetraenide or disodium cyclooctatetraenide. More complex coordination compounds are known as cyclooctatetraenide complexes, such as the actinocenes. The structure is a planar symmetric octagon stabilized by resonance, meaning each atom bears a charge of −. The length of the bond between carbon atoms is 1.432 Å. There are 10 π electrons. The structure can serve as a ligand with various metals. List of salts See also *Tropylium ion In organic chemistry, the tropylium ion or cycloheptatrienyl cation is an aromatic species with a formula of +. Its name derives from the molecule tropine from which cycloheptatriene (tropylidene) was first synthesiz ...
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