Tetrakis(dimethylamino)ethylene
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Tetrakis(dimethylamino)ethylene
Tetrakis(dimethylamino)ethylene (TDAE) is an organic compound with the formula (NMe2)2sub>2 (where Me = CH3). A colorless liquid, this compound is classified as an enamine. Primary and secondary enamines tend to isomerize, but tertiary enamines are kinetically stable. The unusual feature of TDAE is that it is a tetra-enamine. The pi-donating tendency of the amine groups strongly modifies the properties of the molecule, which does exhibit properties of a typical alkene. Reactions TDAE reacts with oxygen in a chemiluminescent reaction to give tetramethylurea TDAE is an electron donor with E = 1.06 V vs Fc+/0. It forms a charge transfer salt with buckminsterfullerene: :C2(N(CH3)2)4 + C60 → 2(N(CH3)2)4+C60−] Oxidation affords a dication. Structure Crystallographic analysis show that TDAE is a highly distorted alkene, the dihedral angle for the two N2C termini is 28″. The C=C distance is alkene-like, 135 pm. The nearly isostructural tetraisopropylethylene also has ...
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Tetramethylurea
Tetramethylurea is the organic compound with the formula (Me2N)2CO. It is a substituted urea. This colorless liquid is used as an aprotic-polar solvent, especially for aromatic compounds and is used e. g. for Grignard reagents. Production The synthesis and properties of tetramethylurea were comprehensively described. The reaction of dimethylamine with phosgene in the presence of e. g. 50 % sodium hydroxide solution and subsequent extraction with 1,2-dichloroethane yields tetramethylurea in 95% yield. The reactions with dimethylcarbamoyl chloride or phosgene are highly exothermic and the removal of the resulting dimethylamine hydrochloride requires some effort. The reaction of diphenylcarbonate with dimethylamine in an autoclave is also effective. Tetramethylurea is formed in the reaction of dimethylcarbamoyl chloride with anhydrous sodium carbonate in a yield of 96.5%. Dimethylcarbamoyl chloride also reacts with excess dimethylamine forming tetramethylurea. Even thoug ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Enamine
An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine. Enamines are versatile intermediates. : The word "enamine" is derived from the affix ''en''-, used as the suffix of alkene, and the root ''amine''. This can be compared with enol, which is a functional group containing both alkene (''en''-) and alcohol (-''ol''). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases. Their behavior as carbon-based nucleophiles is explained with reference to the following reson ...
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Alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, and Biological Chemistry'. 1232 pages. Two general types of monoalkenes are distinguished: terminal and internal. Also called α-olefins, terminal alkenes are more useful. However, the International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc. for cyclic ones; and "olefin" for the general class – cyclic or acyclic, with one or more double bonds. Acyclic alkenes, with only one double bond and no other functional groups (also known as mono-enes) form a homologous series of hydrocarbons with the general formula with '' ...
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Oxygen
Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as well as with other compounds. Oxygen is Earth's most abundant element, and after hydrogen and helium, it is the third-most abundant element in the universe. At standard temperature and pressure, two atoms of the element bind to form dioxygen, a colorless and odorless diatomic gas with the formula . Diatomic oxygen gas currently constitutes 20.95% of the Earth's atmosphere, though this has changed considerably over long periods of time. Oxygen makes up almost half of the Earth's crust in the form of oxides.Atkins, P.; Jones, L.; Laverman, L. (2016).''Chemical Principles'', 7th edition. Freeman. Many major classes of organic molecules in living organisms contain oxygen atoms, such as proteins, nucleic acids, carbohydrates, and fats, as ...
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Chemiluminescence
Chemiluminescence (also chemoluminescence) is the emission of light (luminescence) as the result of a chemical reaction. There may also be limited emission of heat. Given reactants A and B, with an excited intermediate ◊, : + -> lozenge -> roducts+ light For example, if is luminol and is hydrogen peroxide in the presence of a suitable catalyst we have: :\underset + \underset -> 3-APAlozenge-> + light where: * 3-APA is 3-aminophthalate * 3-APA ''◊is the vibronic excited state fluorescing as it decays to a lower energy level. General description The decay of this excited state ''◊to a lower energy level causes light emission. In theory, one photon of light should be given off for each molecule of reactant. This is equivalent to the Avogadro number of photons per mole of reactant. In actual practice, non-enzymatic reactions seldom exceed 1% QC, quantum efficiency. In a chemical reaction, reactants collide to form a transition state, the enthalpic maximum in a r ...
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Oxidation Von TDAE
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a decrease in the oxidation state. There are two classes of redox reactions: * ''Electron-transfer'' – Only one (usually) electron flows from the reducing agent to the oxidant. This type of redox reaction is often discussed in terms of redox couples and electrode potentials. * ''Atom transfer'' – An atom transfers from one substrate to another. For example, in the rusting of iron, the oxidation state of iron atoms increases as the iron converts to an oxide, and simultaneously the oxidation state of oxygen decreases as it accepts electrons released by the iron. Although oxidation reactions are commonly associated with the formation of oxides, other chemical species can serve the same function. In hydrogenation, C=C (and other) bonds ar ...
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Buckminsterfullerene
Buckminsterfullerene is a type of fullerene with the formula C60. It has a cage-like fused-ring structure (truncated icosahedron) made of twenty hexagons and twelve pentagons, and resembles a soccer ball. Each of its 60 carbon atoms is bonded to its three neighbors. Buckminsterfullerene is a black solid that dissolves in hydrocarbon solvents to produce a violet solution. The compound was discovered in 1985 and has received intense study, although few real world applications have been found. Occurrence Buckminsterfullerene is the most common naturally occurring fullerene. Small quantities of it can be found in soot. It also exists in space. Neutral C60 has been observed in planetary nebulae and several types of star. The ionised form, C60+, has been identified in the interstellar medium, where it is the cause of several absorption features known as diffuse interstellar bands in the near-infrared. History Theoretical predictions of buckyball molecules appeared in ...
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Dimethylamino Compounds
Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005. Structure and synthesis The molecule consists of a nitrogen atom with two methyl substituents and one proton. Dimethylamine is a weak base and the pKa of the ammonium CH3--CH3 is 10.73, a value above methylamine (10.64) and trimethylamine (9.79). Dimethylamine reacts with acids to form salts, such as dimethylamine hydrochloride, an odorless white solid with a melting point of 171.5 °C. Dimethylamine is produced by catalytic reaction of methanol and ammonia at elevated temperatures and high pressure: :2 CH3OH + NH3 → (CH3)2NH + 2 H2O Natural occurrence Dimethylamine is found quite widely distributed in animals and plants, and is present in many foods at the level of ...
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