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Phosphine Sulfide
A phosphine sulfide is an organophosphorus compound with the formula R3PS. They are typically colorless, air-stable solids. A common example of a tertiary phosphine sulfide is triphenylphosphine sulfide. Phosphine sulfides are sometimes intermediates in the synthesis of tertiary phosphines. Phosphine sulfides are tetrahedral. Synthesis Phosphine sulfides are usually prepared by the oxidation of tertiary phosphines with elemental sulfur. The heat of formation of phosphine sulfides from tertiary phosphines and elemental sulfur scale with the basicity In chemistry, there are three definitions in common use of the word base, known as Arrhenius bases, Brønsted bases, and Lewis bases. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. Rou ... of the phosphine. {, class="wikitable" , + Enthalpy for sulfiding various tertiary phosphines , - ! Tertiary phosphine !! ∆H (kcal/mol) for reaction with S8 !! Tertiary phosphine s ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tertiary Phosphines
Tertiary ( ) is a widely used but obsolete term for the geologic period from 66 million to 2.6 million years ago. The period began with the demise of the non-avian dinosaurs in the Cretaceous–Paleogene extinction event, at the start of the Cenozoic Era, and extended to the beginning of the Quaternary glaciation at the end of the Pliocene Epoch. The time span covered by the Tertiary has no exact equivalent in the current geologic time system, but it is essentially the merged Paleogene and Neogene periods, which are informally called the Early Tertiary and the Late Tertiary, respectively. The Tertiary established the Antarctic as an icy island continent. Historical use of the term The term Tertiary was first used by Giovanni Arduino during the mid-18th century. He classified geologic time into primitive (or primary), secondary, and tertiary periods based on observations of geology in Northern Italy. Later a fourth period, the Quaternary, was applied. In the early deve ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Basicity
In chemistry, there are three definitions in common use of the word base, known as Arrhenius bases, Brønsted bases, and Lewis bases. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. Rouelle in the mid-18th century. In 1884, Svante Arrhenius proposed that a base is a substance which dissociates in aqueous solution to form Hydroxide ions OH−. These ions can react with hydrogen ions (H+ according to Arrhenius) from the dissociation of acids to form water in an acid–base reaction. A base was therefore a metal hydroxide such as NaOH or Ca(OH)2. Such aqueous hydroxide solutions were also described by certain characteristic properties. They are slippery to the touch, can taste bitter and change the color of pH indicators (e.g., turn red litmus paper blue). In water, by altering the autoionization equilibrium, bases yield solutions in which the hydrogen ion activity is lower than it is in pure water, i.e., the water has ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tricyclohexylphosphine
Tricyclohexylphosphine is the tertiary phosphine with the formula P( C6H11)3. Commonly used as a ligand in organometallic chemistry, it is often abbreviated to PCy3, where Cy stands for cyclohexyl. It is characterized by both high basicity (p''K''a = 9.7) and a large ligand cone angle (170°).{{cite journal , last1 = Immirzi , first1 = A. , last2 = Musco , first2 = A. , title = A Method to Measure the Size of Phosphorus Ligands in Coordination Complexes , doi = 10.1016/S0020-1693(00)95635-4 , year = 1977 , journal = Inorg. Chim. Acta , volume = 25 , pages = L41–42 Important complexes containing P(Cy)3 ligands include the 2005 Nobel Prize-winning Grubbs' catalyst and the homogeneous hydrogenation catalyst Crabtree's catalyst Crabtree's catalyst is an organoiridium compound with the formula ,5-Cyclooctadiene, C8H12IrTricyclohexylphosphine, P(C6H11)3pyridine, C5H5NF6. It is a homogeneous catalyst for hydrogenation and hydrogen-transfer reactions, developed by Rober ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tributylphosphine
Tributylphosphine is the organophosphorus compound with the formula P(CH). Abbreviated or PBu, it is a tertiary phosphine. It is an oily liquid at room temperature, with a nauseating odor. It reacts slowly with atmospheric oxygen, and rapidly with other oxidizing agents, to give the corresponding phosphine oxide. It is usually handled using air-free techniques. Preparation Tributylphosphine is prepared industrially by the hydrophosphination of phosphine with butene: the addition proceeds by a free radical mechanism, and so the Markovnikov rule is not followed. :PH + 3CH=CHCHCH → P(CHCHCHCH) Tributylphosphine can be prepared in the laboratory by reaction of the appropriate Grignard reagent with phosphorus trichloride although, as it is commercially available at reasonable prices, it is rare to have to perform the small-scale preparation. :3 BuMgCl + PCl → PBu + 3 MgCl Reactions Tributylphosphine reacts with oxygen to give the phosphine oxide: :2 PBu3 + O2 → 2 OPBu3 Because ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Trimethylphosphine
Trimethylphosphine is a neutral organophosphorus compound with the formula P(CH3)3, commonly abbreviated as PMe3. This colorless liquid has a strongly unpleasant odor, characteristic of alkylphosphines. The compound is a common ligand in coordination chemistry. Structure and bonding It is a pyramidal molecule with approximate ''C''3''v'' symmetry. The C–P–C bond angles are approximately 98.6°. The C–P–C bond angles are consistent with the notion that phosphorus predominantly uses the 3p orbitals for forming bonds and that there is little sp hybridization of the phosphorus atom. The latter is a common feature of the chemistry of phosphorus. As a result, the lone pair of trimethylphosphine has predominantly s-character as is the case for phosphine, PH3. PMe3 can be prepared by the treatment of triphenyl phosphite with methylmagnesium chloride: : 3 CH3MgCl + P(OC6H5)3 → P(CH3)3 + 3 C6H5OMgCl The synthesis is conducted in dibutyl ether, from which the more volatile PMe3 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dimethylphenylphosphine
Dimethylphenylphosphine is an organophosphorus compound with a formula P(C6H5)(CH3)2. The phosphorus is connected to a phenyl group and two methyl groups, making it the simplest aromatic alkylphosphine. It is colorless air sensitive liquid. It is a member of series (CH3)3-n(C6H5)2P that also includes n = 0, n = 2, and n = 3 that are often employed as ligands in metal phosphine complexes. Preparation Dimethylphenylphosphine is prepared by the reaction of methylmagnesium halide with dichlorophenylphosphine. :(C6H5)Cl2P + 2CH3MgBr → (C6H5)(CH3)2P + 2MgBrCl The phosphine is purified by distillation under reduced pressure. A solution of (C6H5)(CH3)2P in CDCl3 shows proton NMR signals at δ 7.0-7.5 and a doublet at δ 1.2. The phosphorus-31 NMR spectrum shows a singlet at -45.9 ppm in CDCl3. Structure and properties Dimethylphenylphosphine is a pyramidal molecule where the phenyl group and two methyl groups are connected to the phosphorus. The bond length and angles a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diphenylmethylphosphine
Methyldiphenylphosphine is the organophosphine with the formula CH3(C6H5)2P, often abbreviated PMePh2. It is a colorless, viscous liquid. It is a member of series (CH3)3-n(C6H5)2P that also includes n = 0, n = 1, and n = 3 that are often employed as ligands in metal phosphine complexes. Methyldiphenylphosphine is prepared by reaction of chlorodiphenylphosphine with methyl Grignard reagent: :Cl(C6H5)2P + CH3MgBr → CH3(C6H5)2P + MgBrCl Selected derivatives: *The phosphine oxide OPMePh2, prepared by treatment with hydrogen peroxide. *The coordination complex MoH4(PMePh2)4, prepared by treatment of MoCl4(PMePh2)2 with sodium borohydride in the presence of excess ligand. *The coordination complex CoCl2(PMePh2)2, prepared by treating cobalt(II) chloride with the phosphine. *The phosphine-borane In chemistry, phosphine-boranes are organophosphorus compounds with the formula R3−nHnPBH3. They are Lewis acid-Lewis base adducts derived from organophosphines (PR3∠... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
