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Dimethylmercury
Dimethylmercury is an extremely toxic organomercury compound with the formula ( CH3)2 Hg. A volatile, flammable, dense and colorless liquid, dimethylmercury is one of the strongest known neurotoxins. Less than 0.1 mL is capable of inducing severe mercury poisoning resulting in death. Synthesis, structure, and reactions The compound was one of the earliest organometallics reported, reflecting its considerable stability. The compound was first prepared by George Buckton in 1857 by a reaction of methylmercury iodide with potassium cyanide: : 2 CH3HgI + 2 KCN → Hg(CH3)2 + 2 KI + (CN)2 + Hg Later, Edward Frankland discovered that it could be synthesized by treating sodium amalgam with methyl halides: : Hg + 2 Na + 2 CH3I → Hg(CH3)2 + 2 NaI It can also be obtained by alkylation of mercuric chloride with methyllithium: : HgCl2 + 2 LiCH3 → Hg(CH3)2 + 2 LiCl The molecule adopts a linear structure with Hg–C bond lengths of 2.083 Å. Reactivity and physical propert ...
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Mercury Poisoning
Mercury poisoning is a type of metal poisoning due to exposure to mercury. Symptoms depend upon the type, dose, method, and duration of exposure. They may include muscle weakness, poor coordination, numbness in the hands and feet, skin rashes, anxiety, memory problems, trouble speaking, trouble hearing, or trouble seeing. High-level exposure to methylmercury is known as Minamata disease. Methylmercury exposure in children may result in acrodynia (pink disease) in which the skin becomes pink and peels. Long-term complications may include kidney problems and decreased intelligence. The effects of long-term low-dose exposure to methylmercury are unclear. Forms of mercury exposure include metal, vapor, salt, and organic compound. Most exposure is from eating fish, amalgam-based dental fillings, or exposure at a workplace. In fish, those higher up in the food chain generally have higher levels of mercury, a process known as biomagnification. Less commonly, poisoning may occu ...
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Neurotoxin
Neurotoxins are toxins that are destructive to nervous tissue, nerve tissue (causing neurotoxicity). Neurotoxins are an extensive class of exogenous chemical neurological insult (medical), insultsSpencer 2000 that can adversely affect function in both developing and mature nervous tissue.Olney 2002 The term can also be used to classify endogenous compounds, which, when abnormally contacted, can prove neurologically toxic. Though neurotoxins are often neurologically destructive, their ability to specifically target neural components is important in the study of nervous systems. Common examples of neurotoxins include lead, ethanol (drinking alcohol), glutamate,Choi 1987 nitric oxide, botulinum toxin (e.g. Botox), tetanus toxin,Simpson 1986 and tetrodotoxin. Some substances such as nitric oxide and glutamate are in fact essential for proper function of the body and only exert neurotoxic effects at excessive concentrations. Neurotoxins inhibit neuron control over ion concentrations ...
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Mercury (element)
Mercury is a chemical element; it has Symbol (chemistry), symbol Hg and atomic number 80. It is commonly known as quicksilver. A Heavy metal element, heavy, silvery d-block element, mercury is the only metallic element that is known to be liquid at standard temperature and pressure; the only other element that is liquid under these conditions is the halogen bromine, though metals such as caesium, gallium, and rubidium melt just above room temperature. Mercury occurs in deposits throughout the world mostly as cinnabar (mercuric sulfide). The red pigment vermilion is obtained by Mill (grinding), grinding natural cinnabar or synthetic mercuric sulfide. Exposure to mercury and mercury-containing organic compounds is toxic to the nervous system, immune system and kidneys of humans and other animals; mercury poisoning can result from exposure to water-soluble forms of mercury (such as mercuric chloride or methylmercury) either directly or through mechanisms of biomagnification. Mercu ...
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Methylmercury
Methylmercury is an organometallic cation with the formula . It is the simplest organomercury compound. Methylmercury is extremely toxic, and its derivatives are the major source of organic mercury for humans. It is a bioaccumulative environmental toxicant with a 50-day half-life. Methylmercury (derived biologically from dimethylmercury) is the causative agent of the infamous Minamata disease. Methylmercury is designated as a "priority hazardous substance" according to the Directive on Environmental Quality Standards (Directive 2013/39/EU). Structure and chemistry "Methylmercury" is a shorthand for the hypothetical "methylmercury cation", sometimes written ''methylmercury(1+) cation'' or ''methylmercury(II) cation''. This functional group is composed of a methyl group Chemical bond, bonded to an atom of Mercury (element), mercury. Its chemical formula is (sometimes written as ). The Methylmercury compound has an overall charge of +1, with Hg in the +2 oxidation state. Methylmer ...
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Diethylmercury
Diethylmercury is a flammable, colorless liquid, and one of the strongest known neurotoxins. This organomercury compound is described as having a slightly sweet smell, though inhaling enough fumes to notice this would be hazardous. This chemical can cross the blood–brain barrier, causing permanent brain damage. It is, however, considerably less toxic than dimethylmercury. The resulting (CH3CH2)2Hg is a dense liquid (2.466 g/cm3) that boils at 57 °C at 16 torr. This extremely toxic compound is slightly soluble in ethanol and soluble in ether. Synthesis Diethylmercury can be obtained from the reaction between ethylmagnesium bromide and mercury(II) chloride. :2 C2H5MgBr + HgCl2 → Hg(C2H5)2 + MgBr2 + MgCl2 Other methods are also known. See also * Ethylmercury * Mercury poisoning Mercury poisoning is a type of metal poisoning due to exposure to mercury. Symptoms depend upon the type, dose, method, and duration of exposure. They may include muscle weakness, poor ...
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Organomercury Compound
Organomercury chemistry refers to the study of organometallic compounds that contain mercury. Many organomercury compounds are highly toxic, but some are used in medicine, e.g., merbromin ("Mercurochrome") and the vaccine preservative thiomersal. Structure and bonding Most organomercury compounds feature diamagnetic Hg(II) and adopt a linear C-Hg-X structure. Indeed, no organic derivatives of Hg are known, as Hg requires electronegative subtituents for condensed-phase stability. Hg(II) derivatives are neither Lewis basic or Lewis acidic. They are stable to oxygen and water, indicating the low polarity of the Hg-C bond. Mercury forms a compound with two cyclopentadiene ligands, but the resulting complex may not be a metallocene. When made in the 1950s, it was too sensitive for structural determination. Toxicity The toxicity of organomercury compounds presents both dangers and benefits. Dimethylmercury in particular is notoriously toxic, but found use as an antifungal ag ...
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Dimethylmagnesium
Dimethylmagnesium is an organomagnesium compound with the chemical formula . It is a white pyrophoric solid. Dimethylmagnesium is used in the synthesis of organometallic compounds. Preparation Like other dialkylmagnesium compounds, dimethylmagnesium is prepared by adding dioxane to a solution of methylmagnesium halide: : In such procedures, the dimethylmagnesium exists as the ether adduct, not the polymer. Addition of 1,4-dioxane causes precipitation of solid , a coordination polymer. This precipitation drives the Schlenk equilibrium toward . Related methods have been applied to other dialkylmagnesium compounds. Dimethylmagnesium can also be prepared by combining dimethylmercury and magnesium. Calcium metal, magnesium metal and methyl iodide reacts in diethyl ether to produce dimethylmagnesium. : Properties The structure of this compound has been determined by X-ray crystallography. The material is a polymer with the same connectivity as silicon disulfide Silicon disul ...
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Methyl Iodide
Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted in small amounts by rice plantations. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups. Preparation and handling Iodomethane is formed via the exothermic reaction that occurs when iodine is added to a mixture of methanol with red phosphorus. The iodinating reagent is phosphorus triiodide that is formed ''in situ:'' :3 CH3OH + PI3 → 3 CH3I + H2PO3H Alternatively, it is prepared from the reaction of dimethyl sulfate with potassium iodide in the presence of ...
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Redistribution (chemistry)
In chemistry, redistribution usually refers to the exchange of anionic ligands bonded to metal and metalloid centers. The conversion does not involve redox, in contrast to disproportionation reactions. Some useful redistribution reactions are conducted at higher temperatures; upon cooling the mixture, the product mixture is kinetically frozen and the individual products can be separated. In cases where redistribution is rapid at mild temperatures, the reaction is less useful synthetically but still important mechanistically. Examples Redistribution reactions are exhibited by methylboranes. Thus monomethyldiborane rapidly converts at room temperature to diborane and trimethylborane:. The authors refer to redistributions as "disproportionations". :6 MeB2H5 → 5 B2H6 + 2 Me3B Useful redistribution reactions are found in organoaluminium, organoboron, and organosilicon chemistry. : BCl3 + 2 B(C2H5)3 → 3 BCl(C2H5)2 In another example, tetramethylsilane is an undesirable ...
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Volatile Liquids
In chemistry, volatility is a material quality which describes how readily a substance vaporizes. At a given temperature and pressure, a substance with high volatility is more likely to exist as a vapour, while a substance with low volatility is more likely to be a liquid or solid. Volatility can also describe the tendency of a vapor to condense into a liquid or solid; less volatile substances will more readily condense from a vapor than highly volatile ones. Differences in volatility can be observed by comparing how fast substances within a group evaporate (or sublimate in the case of solids) when exposed to the atmosphere. A highly volatile substance such as rubbing alcohol (isopropyl alcohol) will quickly evaporate, while a substance with low volatility such as vegetable oil will remain condensed. In general, solids are much less volatile than liquids, but there are some exceptions. Solids that sublimate (change directly from solid to vapor) such as dry ice (solid carbon dioxi ...
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Alkylation
Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with alkene, olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents. Nucleophilic alkylating agents Nucleophilic alkylating agents deliver the equivalent of an alkyl anion (carbanion). The formal "alkyl anion" attacks an electrophile, forming a new covalent bond ...
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Electronegativity
Electronegativity, symbolized as , is the tendency for an atom of a given chemical element to attract shared electrons (or electron density) when forming a chemical bond. An atom's electronegativity is affected by both its atomic number and the distance at which its valence electrons reside from the charged nucleus. The higher the associated electronegativity, the more an atom or a substituent group attracts electrons. Electronegativity serves as a simple way to quantitatively estimate the bond energy, and the sign and magnitude of a bond's chemical polarity, which characterizes a bond along the continuous scale from covalent to ionic bonding. The loosely defined term electropositivity is the opposite of electronegativity: it characterizes an element's tendency to donate valence electrons. On the most basic level, electronegativity is determined by factors like the nuclear charge (the more protons an atom has, the more "pull" it will have on electrons) and the number and lo ...
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