Dithiol
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Dithiol
In organic chemistry, a dithiol is a type of organosulfur compound with two thiol () functional groups. Their properties are generally similar to those of monothiols in terms of solubility, odor, and volatility. They can be classified according to the relative location of the two thiol groups on the organic backbone. File:C6H4(SH)2.svg, Benzene-1,2-dithiol, the parent aromatic dithiol File:1,3-Propandithiol Structural Formula V1.svg, Propane-1,3-dithiol File:Meso-2,3-dimercaptosuccinic-acid-2D-skeletal-A-configurations-labelled.png, The drug meso-2,3-dimercaptosuccinic acid File:Dimercaprol.svg, Dimercaprol ("British anti-Lewisite"), an early antidote for arsenic poisoning File:Dihydrolipoic-acid-2D-skeletal.png, Dihydrolipoic acid, a vitamin File:Dithiothreitol.png, Dithiothreitol, a reagent in protein biochemistry Geminal dithiols Geminal dithiols have the formula RR'C(SH)2. They are derived from aldehydes and ketones by the action of hydrogen sulfide. Their stability con ...
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Geminal Dithiol
In organic chemistry, a dithiol is a type of organosulfur compound with two thiol () functional groups. Their properties are generally similar to those of monothiols in terms of solubility, odor, and volatility. They can be classified according to the relative location of the two thiol groups on the organic backbone. File:C6H4(SH)2.svg, Benzene-1,2-dithiol, the parent aromatic dithiol File:1,3-Propandithiol Structural Formula V1.svg, Propane-1,3-dithiol File:Meso-2,3-dimercaptosuccinic-acid-2D-skeletal-A-configurations-labelled.png, The drug meso-2,3-dimercaptosuccinic acid File:Dimercaprol.svg, Dimercaprol ("British anti-Lewisite"), an early antidote for arsenic poisoning File:Dihydrolipoic-acid-2D-skeletal.png, Dihydrolipoic acid, a vitamin File:Dithiothreitol.png, Dithiothreitol, a reagent in protein biochemistry Geminal dithiols Geminal dithiols have the formula RR'C(SH)2. They are derived from aldehydes and ketones by the action of hydrogen sulfide. Their stability con ...
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Sodium 1,3-dithiole-2-thione-4,5-dithiolate
Sodium 1,3-dithiole-2-thione-4,5-dithiolate is the organosulfur compound with the formula Na2C3S5, abbreviated Na2dmit. It is the sodium salt of the conjugate base of the 1,3-dithiole-2-thione-4,5-dithiol. The salt is a precursor to dithiolene complexes and tetrathiafulvalenes. Reduction of carbon disulfide with sodium affords sodium 1,3-dithiole-2-thione-4,5-dithiolate together with sodium trithiocarbonate: : 4 Na + 4 CS2 → Na2C3S5 + Na2CS3 Before the characterization of dmit2-, reduction of CS2 was thought to give tetrathiooxalate (Na2C2S4). The dianion C3S52- is purified as the tetraethylammonium salt of the zincate complex n(C3S5)2sup>2-. This salt converts to the bis(thioester) upon treatment with benzoyl chloride: : (C2H5)4sub>2 n(C3S5)2 + 4 C6H5COCl → 2 C3S3(SC(O)C6H5)2 + (C2H5)4sub>2 nCl4Cleavage of the thioester with sodium methoxide Sodium methoxide is the simplest sodium alkoxide. With the formula , it is a white solid, which is formed ...
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Propane-1,3-dithiol
1,3-Propanedithiol is the chemical compound with the formula HSCH2CH2CH2SH. This dithiol is a useful reagent in organic synthesis. This liquid, which is readily available commercially, has an intense stench. Use in organic synthesis 1,3-Propanedithiol is mainly used for the protection of aldehydes and ketones via their reversible formation of dithianes. A prototypical reaction is its formation of 1,3-dithiane from formaldehyde. The reactivity of this dithiane illustrates the concept of umpolung. Alkylation gives thioethers, e.g. 1,5-dithiacyclooctane. The unpleasant odour of 1,3-propanedithiol has encouraged the development of alternative reagents that generate similar derivatives. 1,3-Propanedithiol is used in the synthesis of tiapamil. Use in inorganic synthesis 1,3-Propanedithiol reacts with metal ions to form chelate rings. Illustrative is the synthesis of the derivative diiron propanedithiolate hexacarbonyl upon reaction with triiron dodecacarbonyl Triiron dod ...
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1,2-Benzenedithiol
Benzene-1,2-dithiol is the organosulfur compound with the formula CH(SH). This colourless viscous liquid consists of a benzene ring with a pair of adjacent thiol groups. The conjugate base of this diprotic compound serves as chelating agent in coordination chemistry and a building block for the synthesis of other organosulfur compounds.Karlin, K. D.; Stiefel, E. I., Eds. “Progress in Inorganic Chemistry, Dithiolene Chemistry: Synthesis, Properties, and Applications” Wiley-Interscience: New York, 2003. Synthesis The compound is prepared by ortho-lithiation of benzenethiol using butyl lithium (BuLi) followed by sulfidation: :CHSH + 2 BuLi → CHSLi-2-Li + 2 BuH :CHSLi-2-Li + S → CH(SLi) :CH(SLi) + 2 HCl → CH(SH) + 2 LiCl The compound was first prepared from 2-aminobenzenethiol via diazotization. Alternatively, it forms from 1,2-dibromobenzene. Reactions Oxidation mainly affords the polymeric disulfide. Reaction with metal dihalides and metal oxides gives the dithiolate ...
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Methanedithiol
Methanedithiol is an organosulfur compound with the formula H2C(SH)2. It forms when formaldehyde is treated with hydrogen sulfide under pressure. The reaction competes with formation of trithiane. The compound forms a solid dibenzoate upon treatment with benzoic anhydride.{{cite journal, title=gem-Dithiols, authors=Cairns, T. L.; Evans, G. L.; Larchar, A. W.; McKusick, B. C., journal=Journal of the American Chemical Society, year=1952, volume=74, issue=16, pages=3982–9, doi=10.1021/ja01136a004 References Thiols Functional groups Organosulfur compounds Foul-smelling chemicals ...
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Benzene-1,2-dithiol
Benzene-1,2-dithiol is the organosulfur compound with the formula CH(SH). This colourless viscous liquid consists of a benzene ring with a pair of adjacent thiol groups. The conjugate base of this diprotic compound serves as chelating agent in coordination chemistry and a building block for the synthesis of other organosulfur compounds.Karlin, K. D.; Stiefel, E. I., Eds. “Progress in Inorganic Chemistry, Dithiolene Chemistry: Synthesis, Properties, and Applications” Wiley-Interscience: New York, 2003. Synthesis The compound is prepared by ortho-lithiation of benzenethiol using butyl lithium (BuLi) followed by sulfidation: :CHSH + 2 BuLi → CHSLi-2-Li + 2 BuH :CHSLi-2-Li + S → CH(SLi) :CH(SLi) + 2 HCl → CH(SH) + 2 LiCl The compound was first prepared from 2-aminobenzenethiol via diazotization. Alternatively, it forms from 1,2-dibromobenzene. Reactions Oxidation mainly affords the polymeric disulfide. Reaction with metal dihalides and metal oxides gives the dithiolate ...
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Dithiane
A dithiane is a heterocyclic compound composed of a cyclohexane core structure wherein two methylene bridges (-- units) are replaced by sulfur centres. The three isomeric parent heterocycles are 1,2-dithiane, 1,3-dithiane and 1,4-dithiane. 1,3-Dithianes 1,3-Dithianes are protecting group of some carbonyl-containing compounds due to their inertness to many conditions. They form by treatment of the carbonyl compound with 1,3-propanedithiol under conditions that remove water from the system. The protecting group can be removed with mercuric reagents, a process that exploits the high affinity of Hg(II) for thiolates. 1,3-Dithianes are also employed in umpolung reactions, such as the Corey–Seebach reaction:T. W. Green, P. G. M. Wuts, "Protective Groups in Organic Synthesis" Wiley-Interscience, New York, 1999. . : Typically, in organic synthesis, ketones and aldehydes are protected as their dioxolane Dioxolane is a heterocyclic acetal with the chemical formula (CH2)2O2CH2. ...
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Chelation Therapy
Chelation therapy is a medical procedure that involves the administration of Chelation, chelating agents to remove heavy metals from the body. Chelation therapy has a long history of use in clinical toxicology and remains in use for some very specific medical treatments, although it is administered under very careful medical supervision due to various inherent risks, including the mobilization of mercury and other metals through the brain and other parts of the body by the use of weak chelating agents that unbind with metals before elimination, exacerbating existing damage. To avoid mobilization, some practitioners of chelation use strong chelators, such as selenium, taken at low doses over a long period of time. Chelation therapy must be administered with care as it has a number of possible side effects, including death. In response to increasing use of chelation therapy as alternative medicine and in circumstances in which the therapy should not be used in conventional medicine ...
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2,3-Dimercapto-1-propanesulfonic Acid
2,3-Dimercapto-1-propanesulfonic acid (abbreviated DMPS) and its sodium salt (known as Unithiol) are chelating agents that form complexes with various heavy metals. They are related to dimercaprol, which is another chelating agent. The synthesis of DMPS was first reported in 1956 by V. E. Petrunkin. The effects of DMPS on heavy metal poisoning, including with polonium-210, were investigated in the following years. DMPS was found to have some protective effect, prolonging the survival time. A study was undertaken of DMPS use by workers involved in the production of a calomel skin bleaching lotion and in direct contact with mercurous chloride and that already showed elevated urine mercury levels. The sodium salt of DMPS was found to be effective in lowering the body burden of mercury and in decreasing the urinary mercury concentration to normal levels. DMPS administrated to a mercury poisoned animal model failed to remove the mercury from tissues and reduce the inorganic mercury ...
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Dimercaprol
Dimercaprol, also called British anti-Lewisite (BAL), is a medication used to treat acute poisoning by arsenic, mercury, gold, and lead. It may also be used for antimony, thallium, or bismuth poisoning, although the evidence for those uses is not very strong. It is given by injection into a muscle. Common side effects include high blood pressure, pain at the site of the injection, vomiting, and fever. It is not recommended for people with peanut allergies as it is typically formulated as a suspension in peanut oil. It is unclear if use in pregnancy is safe for the baby. Dimercaprol is a chelator and works by binding with heavy metals. It has a very pungent odor. Dimercaprol was first made during World War II. It is on the World Health Organization's List of Essential Medicines. Medical uses Dimercaprol has long been the mainstay of chelation therapy for lead or arsenic poisoning, and it is an essential drug. It is also used as an antidote to the chemical weapon Lewisite. Non ...
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Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical ( in silico) study. The range of chemicals studied in organic chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but also containing other elements, especially oxygen, nitrogen, sulfur, phosphorus (included in ...
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Oligomer
In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relative molecular mass, the structure of which essentially comprises a small plurality of units derived, actually or conceptually, from molecules of lower relative molecular mass.'' The name is composed of Greek elements '' oligo-'', "a few" and '' -mer'', "parts". An adjective form is ''oligomeric''. The oligomer concept is contrasted to that of a polymer, which is usually understood to have a large number of units, possibly thousands or millions. However, there is no sharp distinction between these two concepts. One proposed criterion is whether the molecule's properties vary significantly with the removal of one or a few of the units. An oligomer with a specific number of units is referred to by the Greek prefix denoting that number, wi ...
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