Tetramethylthiuram Sulfide
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Tetramethylthiuram Sulfide
Tetramethylthiuram sulfide is an organosulfur compound with the formula ((CH3)2NCS)2S. It is a yellow solid that is soluble in organic solvents. It is the parent member of a large class of tetraalkylthiuram sulfides. It is used as an activator in the sulfur vulcanization of natural and butyl rubbers. Synthesis and structure It is prepared by desulfuration of tetramethylthiuram disulfides with triphenylphosphine or cyanide: :(Me2NCSS)2 + PPh3 → (Me2NCS)2S + SPPh3 According to X-ray crystallography, the molecule consists of two planar (CH3)2NCS subunits joined by a sulfide. The dihedral angle A dihedral angle is the angle between two intersecting planes or half-planes. In chemistry, it is the clockwise angle between half-planes through two sets of three atoms, having two atoms in common. In solid geometry, it is defined as the uni ... between the subunits is close to 90°. References Organosulfur compounds {{organic-compound-stub ...
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Organosulfur Compound
Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfur is vital for life. Of the 20 common amino acids, two ( cysteine and methionine) are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal, petroleum, and natural gas, which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries. Sulfur shares the chalcogen group with oxygen, selenium, and tellurium, and it is expected that organosulfur compounds have similarities with carbon–oxygen, carbon–selenium, and carbon–tellurium compounds. A classical chemical test for the detection of sulfur co ...
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Sulfur Vulcanization
Sulfur vulcanization is a chemical process for converting natural rubber or related polymers into materials of varying hardness, elasticity, and mechanical durability by heating them with sulfur or sulfur-containing compounds. Sulfur forms cross-linking bridges between sections of polymer chains which affects the mechanical and electronic properties. Many products are made with vulcanized rubber, including tires, shoe soles, hoses, and conveyor belts. The term is derived from Vulcan, the Roman god of fire. The main polymers subjected to sulfur vulcanization are polyisoprene (natural rubber, NR), polybutadiene rubber (BR) and styrene-butadiene rubber (SBR), and ethylene propylene diene monomer rubber ( EPDM rubber). All of these materials contain alkene groups adjacent to methylene groups. Other specialty rubbers may also be vulcanized, such as nitrile rubber (NBR) and butyl rubber (IIR). Vulcanization, in common with the curing of other thermosetting polymers, is generally ...
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Thiuram Disulfide
Thiuram disulfides are a class of organosulfur compounds with the formula (R2NCSS)2. Many examples are known, but popular ones include R = Me and Et. They are disulfides obtained by oxidation of the dithiocarbamates. These compounds are used in sulfur vulcanization of rubber as well as pesticides and drugs. They are typically white or pale yellow solids that are soluble in organic solvents. Preparation, structure, reactions They are prepared by the oxidation of the salts of the corresponding dithiocarbamates (e.g. sodium diethyldithiocarbamate). Typical oxidants are chlorine and hydrogen peroxide: :2 R2NCSSNa + Cl2 → (R2NCSS)2 + 2 NaCl Thiuram disulfides react with Grignard reagents to give esters of dithiocarbamic acid, as in the preparation of methyl dimethyldithiocarbamate: : e2NC(S)Ssub>2 + MeMgX → Me2NC(S)SMe + Me2NCS2MgX The compounds feature planar dithiocarbamate subunits and are linked by an S−S bond of 2.00  Å. The C(S)−N bond is sh ...
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Triphenylphosphine
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to P Ph3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether. Preparation and structure Triphenylphosphine can be prepared in the laboratory by treatment of phosphorus trichloride with phenylmagnesium bromide or phenyllithium. The industrial synthesis involves the reaction between phosphorus trichloride, chlorobenzene, and sodium: :PCl3 + 3 PhCl + 6 Na → PPh3 + 6 NaCl Triphenylphosphine crystallizes in triclinic and monoclinic modification. In both cases, the molecule adopts a pyramidal structure with propeller-like arrangement of the three phenyl groups. Principal reactions with chalcogens, halogens, and acids Oxidation Triphenylphosphine undergoes slow ...
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Cyanide
Cyanide is a naturally occurring, rapidly acting, toxic chemical that can exist in many different forms. In chemistry, a cyanide () is a chemical compound that contains a functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom. In inorganic cyanides, the cyanide group is present as the anion . Soluble salts such as sodium cyanide (NaCN) and potassium cyanide (KCN) are highly toxic. Hydrocyanic acid, also known as hydrogen cyanide, or HCN, is a highly volatile liquid that is produced on a large scale industrially. It is obtained by acidification of cyanide salts. Organic cyanides are usually called nitriles. In nitriles, the group is linked by a covalent bond to carbon. For example, in acetonitrile (), the cyanide group is bonded to methyl (). Although nitriles generally do not release cyanide ions, the cyanohydrins do and are thus rather toxic. Bonding The cyanide ion is isoelectronic with carbon monoxide a ...
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Triphenylphosphine Sulfide
Triphenylphosphine sulfide (IUPAC name: triphenyl-''λ''5-phosphanethione) is the organophosphorus compound with the formula , usually written (where Ph = phenyl). It is a colourless solid, which is soluble in a variety of organic solvents. Structurally, the molecule resembles the corresponding oxide, with idealized C3 symmetry group, point group symmetry. It is weakly nucleophilic at the sulfur atom. Applications Organic synthesis Triphenylphosphine sulfide is useful for the conversion of epoxides to the corresponding episulfides: : Analytical chemistry In analytical chemistry, triphenylphosphine is used for the analysis of certain kinds of sulfur compounds. Elemental sulfur (), as occurs in some oils, and labile organosulfur compounds, such as organic trisulfides, react with triphenylphosphine to give , which can be detected by gas chromatography. References

{{reflist Organophosphine sulfides Phenyl compounds ...
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X-ray Crystallography
X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles and intensities of these diffracted beams, a crystallographer can produce a three-dimensional picture of the density of electrons within the crystal. From this electron density, the mean positions of the atoms in the crystal can be determined, as well as their chemical bonds, their crystallographic disorder, and various other information. Since many materials can form crystals—such as salts, metals, minerals, semiconductors, as well as various inorganic, organic, and biological molecules—X-ray crystallography has been fundamental in the development of many scientific fields. In its first decades of use, this method determined the size of atoms, the lengths and types of chemical bonds, and the atomic-scale differences among various mat ...
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Sulfide
Sulfide (British English also sulphide) is an inorganic anion of sulfur with the chemical formula S2− or a compound containing one or more S2− ions. Solutions of sulfide salts are corrosive. ''Sulfide'' also refers to chemical compounds large families of inorganic and organic compounds, e.g. lead sulfide and dimethyl sulfide. Hydrogen sulfide (H2S) and bisulfide (SH−) are the conjugate acids of sulfide. Chemical properties The sulfide ion, S2−, does not exist in aqueous alkaline solutions of Na2S. Instead sulfide converts to hydrosulfide: :S2− + H2O → SH− + OH− Upon treatment with an acid, sulfide salts convert to hydrogen sulfide: :S2− + H+ → SH− :SH− + H+ → H2S Oxidation of sulfide is a complicated process. Depending on the conditions, the oxidation can produce elemental sulfur, polysulfides, polythionates, sulfite, or sulfate. Metal sulfides react with halogens, forming sulfur and metal salts. :8 MgS + 8 I2 → S8 + 8 M ...
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Dihedral Angle
A dihedral angle is the angle between two intersecting planes or half-planes. In chemistry, it is the clockwise angle between half-planes through two sets of three atoms, having two atoms in common. In solid geometry, it is defined as the union of a line and two half-planes that have this line as a common edge. In higher dimensions, a dihedral angle represents the angle between two hyperplanes. The planes of a flying machine are said to be at positive dihedral angle when both starboard and port main planes (commonly called wings) are upwardly inclined to the lateral axis. When downwardly inclined they are said to be at a negative dihedral angle. Mathematical background When the two intersecting planes are described in terms of Cartesian coordinates by the two equations : a_1 x + b_1 y + c_1 z + d_1 = 0 :a_2 x + b_2 y + c_2 z + d_2 = 0 the dihedral angle, \varphi between them is given by: :\cos \varphi = \frac and satisfies 0\le \varphi \le \pi/2. Alternatively, if an ...
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