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Hexaphenylcarbodiphosphorane
Hexaphenylcarbodiphosphorane is the organophosphorus compound with the formula C(PPh3)2 (where Ph = C6H5). It is a yellow, moisture-sensitive solid. The compound is classified as an ylide and as such carries significant negative charge on carbon. It is isoelectronic with bis(triphenylphosphine)iminium. The P-C-P angle is 131°. The compound has attracted attention as an unusual ligand in organometallic chemistry. The pure compound has two crystalline phases: a metastable monoclinic C2 phase that is triboluminescent, and an orthorhombic P222 form that is not. Both polymorphs are photoluminescent, with respective peak wavelengths at 540 and 575 nm. Preparation The compound was originally prepared by deprotonation of the phosphonium salt C(PPh3)2r using potassium. An improved procedure entails production of the same double phosphonium salt from methylene bromide. The double deprotonation is effected with potassium amide.{{cite journal , doi=10.1016/j.ica.2017.04.018, ti ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bis(triphenylphosphine)iminium Chloride
Bis(triphenylphosphine)iminium chloride is the chemical compound with the formula , often abbreviated , where Ph is phenyl , or even abbreviated PNl or NPl or PPNCl or PNPCl, where PPN or PNP stands for . This colorless salt is a source of the cation (abbreviated or ), which is used as an unreactive and weakly coordinating cation to isolate reactive anions. is a phosphazene. Synthesis and structure is prepared in two steps from triphenylphosphine : : This triphenylphosphine dichloride is related to phosphorus pentachloride . Treatment of this species with hydroxylamine in the presence of results in replacement of the two single P–Cl bonds in by one double P=N bond: : Triphenylphosphine oxide is a by-product. Bis(triphenylphosphine)iminium chloride is described as . The structure of the bis(triphenylphosphine)iminium cation is . The P=N=P angle in the cation is flexible, ranging from ~130 to 180° depending on the salt. Bent and linear forms of the P=N=P connections ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Wittig Reagent
In organic chemistry, Wittig reagents are organophosphorus compounds of the formula R3P=CHR', where R is usually phenyl. They are used to convert ketones and aldehydes to alkenes: : Preparation Because they typically hydrolyze and oxidize readily, Wittig reagents are prepared using air-free techniques. They are typically generated and used in situ. THF is a typical solvent. Some are sufficiently stable to be sold commercially. ;Formation of phosphonium salt Wittig reagents are usually prepared from a phosphonium salt, which is in turn prepared by the quaternization of triphenylphosphine with an alkyl halide. Wittig reagents are usually derived from a primary alkyl halide. Quaternization of triphenylphosphine with secondary halides is typically inefficient. For this reason, Wittig reagents are rarely used to prepare tetrasubstituted alkenes. ;Bases for deprotonation of phosphonium salts The alkylphosphonium salt is deprotonated with a strong base such as ''n''-butyllithium: : ... [...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] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ylide
An ylide or ylid () is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both atoms have full octets of electrons. The result can be viewed as a structure in which two adjacent atoms are connected by both a covalent and an ionic bond; normally written X+–Y−. Ylides are thus 1,2-dipolar compounds, and a subclass of zwitterions. They appear in organic chemistry as reagents or reactive intermediates. The class name "ylide" for the compound should not be confused with the suffix "-ylide". Resonance structures Many ylides may be depicted by a multiple bond form in a resonance structure, known as the ylene form, while the actual structure lies in between both forms: : The actual bonding picture of these types of ylides is strictly zwitterionic (the structure on the right) with the strong Coulombic attraction between the " ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Monoclinic
In crystallography, the monoclinic crystal system is one of the seven crystal systems. A crystal system is described by three vectors. In the monoclinic system, the crystal is described by vectors of unequal lengths, as in the orthorhombic system. They form a parallelogram prism. Hence two pairs of vectors are perpendicular (meet at right angles), while the third pair makes an angle other than 90°. Bravais lattices Two monoclinic Bravais lattices exist: the primitive monoclinic and the base-centered monoclinic. For the base-centered monoclinic lattice, the primitive cell has the shape of an oblique rhombic prism;See , row mC, column Primitive, where the cell parameters are given as a1 = a2, α = β it can be constructed because the two-dimensional centered rectangular base layer can also be described with primitive rhombic axes. Note that the length a of the primitive cell below equals \frac \sqrt of the conventional cell above. Crystal classes The table below org ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triboluminescent
Triboluminescence is a phenomenon in which light is generated when a material is mechanically pulled apart, ripped, scratched, crushed, or rubbed (see tribology). The phenomenon is not fully understood, but appears to be caused by the separation and reunification of static electrical charges. The term comes from the Greek τρίβειν ("to rub"; see tribology) and the Latin ''lumen'' (light). Triboluminescence can be observed when breaking sugar crystals and peeling adhesive tapes. ''Triboluminescence'' is often used as a synonym for ''fractoluminescence'' (a term sometimes used when referring only to light emitted from fractured crystals). Triboluminescence differs from piezoluminescence in that a piezoluminescent material emits light when it is deformed, as opposed to broken. These are examples of mechanoluminescence, which is luminescence resulting from any mechanical action on a solid. History Uncompahgre Ute indigenous people The Uncompahgre Ute indigenous people ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Orthorhombic
In crystallography, the orthorhombic crystal system is one of the 7 crystal systems. Orthorhombic lattices result from stretching a cubic lattice along two of its orthogonal pairs by two different factors, resulting in a rectangular prism with a rectangular base (''a'' by ''b'') and height (''c''), such that ''a'', ''b'', and ''c'' are distinct. All three bases intersect at 90° angles, so the three lattice vectors remain mutually orthogonal. Bravais lattices There are four orthorhombic Bravais lattices: primitive orthorhombic, base-centered orthorhombic, body-centered orthorhombic, and face-centered orthorhombic. For the base-centered orthorhombic lattice, the primitive cell has the shape of a right rhombic prism;See , row oC, column Primitive, where the cell parameters are given as a1 = a2, α = β = 90° it can be constructed because the two-dimensional centered rectangular base layer can also be described with primitive rhombic axes. Note that the length a of the primit ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Photoluminescent
Photoluminescence (abbreviated as PL) is light emission from any form of matter after the absorption of photons (electromagnetic radiation). It is one of many forms of luminescence (light emission) and is initiated by photoexcitation (i.e. photons that excite electrons to a higher energy level in an atom), hence the prefix ''photo-''. Following excitation, various relaxation processes typically occur in which other photons are re-radiated. Time periods between absorption and emission may vary: ranging from short femtosecond-regime for emission involving free-carrier plasma in inorganic semiconductorsHayes, G.R.; Deveaud, B. (2002). "Is Luminescence from Quantum Wells Due to Excitons?". ''Physica Status Solidi A'' 190 (3): 637–640doi:10.1002/1521-396X(200204)190:33.0.CO;2-7/ref> up to milliseconds for phosphoresence processes in molecular systems; and under special circumstances delay of emission may even span to minutes or hours. Observation of photoluminescence at a certain en ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phosphonium Salt
In polyatomic cations with the chemical formula (where R is a hydrogen or an alkyl, aryl, or halide group). These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions. Types of phosphonium cations Protonated phosphines The parent phosphonium is as found in the iodide salt, phosphonium iodide. Salts of the parent are rarely encountered, but this ion is an intermediate in the preparation of the industrially useful tetrakis(hydroxymethyl)phosphonium chloride: :PH3 + HCl + 4 CH2O → Many organophosphonium salts are produced by protonation of primary, secondary, and tertiary phosphines: :PR3 + H+ → The basicity of phosphines follows the usual trends, with R = alkyl being more basic than R = aryl. Tetraorganophosphonium cations The most common phosphonium compounds have four organic substituents attached to phosphorus. The quaternary phosphonium cations include tetraphenylphosphonium, (C6H5)4P+ and tetramethylphosphonium ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Potassium Amide
Potassium amide is an inorganic compound with the chemical formula . Like other alkali metal amides, it is a white solid that hydrolyzes readily. It is a strong base. Production Potassium amide is produced by the reaction of ammonia with potassium. The reaction typically requires a catalyst. Structure Traditionally is viewed as a simple salt, but it has significant covalent character and is highly aggregated in ammonia solution. The compound has been characterized by 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 ... as the solvent-free form as well as the mono- and diammonia solvates. In , the potassium centers are each bonded to two amido ligands and four ammonia ligands, all six of which bridge to adjacent potassium centers. The result is a chain of hexacoo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methylenetriphenylphosphorane
Methylenetriphenylphosphorane is an organophosphorus compound with the formula Ph3PCH2. It is the parent member of the phosphorus ylides, popularly known as Wittig reagents. It is a highly polar, highly basic species. Preparation and use Methylenetriphenylphosphorane is prepared from methyltriphenylphosphonium bromide by its deprotonation using a strong base like butyllithium: :Ph3PCH3Br + BuLi → Ph3PCH2 + LiBr + BuH The phosphorane is generally not isolated, instead it is used in situ. The estimated pKa of this carbon acid is near 15. Potassium tert-butoxide has been used in place of butyl lithium. Sodium amide has also been used a base. Methylenetriphenylphosphorane is used to replace oxygen centres in aldehydes and ketones with a methylene group, i.e., a methylenation: :R2CO + Ph3PCH2 → R2C=CH2 + Ph3PO The phosphorus-containing product is triphenylphosphine oxide. Structure Crystallographic characterization of the colourless ylide reveals that the phosphorus atom is approx ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
