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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 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 Gas chromatography (GC) is a common type of chromatography used in analytical chemistry for separating and analyzing compounds that can be ...
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Triphenylphosphine Oxide
Triphenylphosphine oxide (often abbreviated TPPO) is the organophosphorus compound with the formula OP(C6H5)3, also written as Ph3PO or PPh3O (Ph = C6H5). This colourless crystalline compound is a common but potentially useful waste product in reactions involving triphenylphosphine. It is a popular reagent to induce the crystallizing of chemical compounds. Structure and properties Ph3PO is a tetrahedral molecule related to POCl3. The oxygen center is relatively basic. The rigidity of the backbone and the basicity of the oxygen center make this species a popular agent to crystallize otherwise difficult to crystallize molecules. This trick is applicable to molecules that have acidic hydrogen atoms, e.g. phenols. Up to now, several modifications of Ph3PO have been found: For example, a monoclinic form crystalizes in the space group ''P''21/''c'' with Z = 4 and a = 15.066(1) Å, b = 9.037(2) Å, c = 11.296(3) Å, and β = 98.47(1)°. The orthorhombic modification crystallizes in ...
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IUPAC
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is a member of the International Science Council (ISC). IUPAC is registered in Zürich, Switzerland, and the administrative office, known as the "IUPAC Secretariat", is in Research Triangle Park, North Carolina, United States. This administrative office is headed by IUPAC's executive director, currently Lynn Soby. IUPAC was established in 1919 as the successor of the International Congress of Applied Chemistry for the advancement of chemistry. Its members, the National Adhering Organizations, can be national chemistry societies, national academies of sciences, or other bodies representing chemists. There are fifty-four National Adhering Organizations and three Associate National Adhering Organizations. IUPAC's Inter-divisional Committee o ...
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Organophosphorus Compound
Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents. Organophosphorus chemistry is the corresponding science of the properties and reactivity of organophosphorus compounds. Phosphorus, like nitrogen, is in group 15 of the periodic table, and thus phosphorus compounds and nitrogen compounds have many similar properties. The definition of organophosphorus compounds is variable, which can lead to confusion. In industrial and environmental chemistry, an organophosphorus compound need contain only an organic substituent, but need not have a direct phosphorus-carbon (P-C) bond. Thus a large proportion of pesticides (e.g., malathion), are often included in this class of compounds. Phosphorus can adopt ...
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Phenyl
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a functional group. Phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring. Nomenclature Usually, a "phenyl group" is synonymous with C6H5− and is represented by the symbol Ph or, archaically, Φ. Benzene is sometimes denoted as PhH. Phenyl groups are generally attached to other atoms or groups. For example, triphenylmethane (Ph3 ...
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Symmetry Group
In group theory, the symmetry group of a geometric object is the group of all transformations under which the object is invariant, endowed with the group operation of composition. Such a transformation is an invertible mapping of the ambient space which takes the object to itself, and which preserves all the relevant structure of the object. A frequent notation for the symmetry group of an object ''X'' is ''G'' = Sym(''X''). For an object in a metric space, its symmetries form a subgroup of the isometry group of the ambient space. This article mainly considers symmetry groups in Euclidean geometry, but the concept may also be studied for more general types of geometric structure. Introduction We consider the "objects" possessing symmetry to be geometric figures, images, and patterns, such as a wallpaper pattern. For symmetry of physical objects, one may also take their physical composition as part of the pattern. (A pattern may be specified formally as a scalar fiel ...
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Acta Crystallographica Section B
''Acta Crystallographica'' is a series of peer-reviewed scientific journals, with articles centred on crystallography, published by the International Union of Crystallography (IUCr). Originally established in 1948 as a single journal called ''Acta Crystallographica'', there are now six independent ''Acta Crystallographica'' titles: *'' Acta Crystallographica Section A: Foundations and Advances'' *'' Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials'' *'' Acta Crystallographica Section C: Structural Chemistry'' *'' Acta Crystallographica Section D: Structural Biology'' *'' Acta Crystallographica Section E: Crystallographic Communications'' *'' Acta Crystallographica Section F: Structural Biology Communications'' ''Acta Crystallographica'' has been noted for the high quality of the papers that it produces, as well as the large impact that its papers have had on the field of crystallography. The current six journals form part of the journal port ...
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Nucleophilic
In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are Lewis bases. ''Nucleophilic'' describes the affinity of a nucleophile to bond with positively charged atomic nuclei. Nucleophilicity, sometimes referred to as nucleophile strength, refers to a substance's nucleophilic character and is often used to compare the affinity of atoms. Neutral nucleophilic reactions with solvents such as alcohols and water are named solvolysis. Nucleophiles may take part in nucleophilic substitution, whereby a nucleophile becomes attracted to a full or partial positive charge, and nucleophilic addition. Nucleophilicity is closely related to basicity. History The terms ''nucleophile'' and '' electrophile'' were introduced by Christopher Kelk Ingold in 1933, replacing the terms ''anionoid'' and ''cationoid ...
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Epoxide
In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile. Nomenclature A compound containing the epoxide functional group can be called an epoxy, epoxide, oxirane, and ethoxyline. Simple epoxides are often referred to as oxides. Thus, the epoxide of ethylene (C2H4) is ethylene oxide (C2H4O). Many compounds have trivial names; for instance, ethylene oxide is called "oxirane". Some names emphasize the presence of the epoxide functional group, as in the compound ''1,2-epoxyheptane'', which can also be called ''1,2-heptene oxide''. A polymer formed from epoxide precursors is called an ''epoxy'', but such materials do not contain epoxide groups (or contain only a few residual epoxy ...
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Episulfide
In organic chemistry, episulfides are a class of organic compounds that contain a saturated, heterocyclic ring consisting of two carbon atoms and one sulfur atom. It is the sulfur analogue of an epoxide or aziridine. They are also known as thiiranes, olefin sulfides, thioalkylene oxides, and thiacyclopropanes. Episulfides are less common and generally less stable than epoxides. The most common derivative is ethylene sulfide (). Structure According to electron diffraction, the and distances in ethylene sulfide are respectively 1.473 and 1.811  Å. The and angles are respectively 66.0 and 48.0°. Preparation History A number of chemists in the early 1900s, including Staudinger and Pfenninger (1916), as well as Delepine (1920) studied episulfides.Sander, M. Thiiranes. Chem. Rev. 1966, 66(3), 297-339. I 1934 Dachlauer and Jackel devised a general synthesis of episulfides from epoxides using alkali thiocyanates and thiourea. Contemporary methods Following the lead of Da ...
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Analytical Chemistry
Analytical chemistry studies and uses instruments and methods to separate, identify, and quantify matter. In practice, separation, identification or quantification may constitute the entire analysis or be combined with another method. Separation isolates analytes. Qualitative analysis identifies analytes, while quantitative analysis determines the numerical amount or concentration. Analytical chemistry consists of classical, wet chemical methods and modern, instrumental methods. Classical qualitative methods use separations such as precipitation, extraction, and distillation. Identification may be based on differences in color, odor, melting point, boiling point, solubility, radioactivity or reactivity. Classical quantitative analysis uses mass or volume changes to quantify amount. Instrumental methods may be used to separate samples using chromatography, electrophoresis or field flow fractionation. Then qualitative and quantitative analysis can be performed, often with ...
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Organosulfur Compounds
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 ...
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Trisulfide
In organic and organometallic chemistry, trisulfide is the functional group R-S-S-S-R. Examples include: * Diallyl trisulfide * Dimethyl trisulfide * Trisulfane (hydrogen trisulfide) Some inorganic compounds are also named trisulfides to reflect their stoichiometry. Examples include: * Antimony trisulfide * Arsenic trisulfide Arsenic trisulfide is the inorganic compound with the formula . It is a dark yellow solid that is insoluble in water. It also occurs as the mineral orpiment (Latin: auripigmentum), which has been used as a pigment called King's yellow. It is produc ... * Bismuth trisulfide * Dibismuth trisulfide * Diboron trisulfide * Diiron trisulfide * Molybdenum trisulfide * Phosphorus trisulfide {{chemistry index ...
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