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Tetraphenylborate
Tetraphenylborate (IUPAC name: Tetraphenylboranuide) is an organoboron anion consisting of a central boron atom with four phenyl groups. Salts of tetraphenylborate uncouple oxidative phosphorylation Oxidative phosphorylation (UK , US ) or electron transport-linked phosphorylation or terminal oxidation is the metabolic pathway in which cells use enzymes to oxidize nutrients, thereby releasing chemical energy in order to produce adenosine t .... See also * Sodium tetraphenylborate * Potassium tetraphenylborate * Triphenylborane * BARF and other fluorinated derivatives are used as non-coordinating anions. References Anions {{chemistry-stub ...
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Sodium Tetraphenylborate
Sodium tetraphenylborate is the organic compound with the formula NaB(C6H5)4. It is a salt, wherein the anion consists of four phenyl rings bonded to boron. This white crystalline solid is used to prepare other tetraphenylborate salts, which are often highly soluble in organic solvents. The compound is used in inorganic and organometallic chemistry as a precipitating agent for potassium, ammonium, rubidium, and cesium ions, and some organic nitrogen compounds. Synthesis and structure Sodium tetraphenylborate is synthesized by the reaction between sodium tetrafluoroborate and phenylmagnesium bromide: :NaBF4 + 4 PhMgBr → 2 MgBr2 + 2 MgF2 + NaBPh4 (where Ph = phenyl) A related synthesis involves the use of phenylsodium in place of the Grignard reagent. Unlike smaller counteranions, such as nitrate and the halides, tetraphenylborate confers lipophilicity to its salts. Many analogous tetraarylborates have been synthesized, containing both electron-rich and electron-defici ...
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Potassium Tetraphenylborate
Potassium tetraphenylborate is the salt with the formula KB(C6H5)4). It is a colourless salt that is a rare example of a water-insoluble salt of potassium. The salt has a low solubility in water of only 1.8×10−4 g/L. It is, however, soluble in organic solvents. The insolubility of this compound has been used to determine the concentration of potassium ions by precipitation and gravimetric analysis: : K+ + NaB(Ph)4 → KB(Ph)4 + Na+ The compound adopts a polymeric structure with bonds between the phenyl rings and potassium. As such it is classified as an organopotassium compound Organosodium chemistry is the chemistry of organometallic compounds containing a carbon to sodium chemical bond. The application of organosodium compounds in chemistry is limited in part due to competition from organolithium compounds, which are ....Ulrich Behrens, Frank Hoffmann, and Falk Olbrich "Solid-State Structures of Base-Free Lithium and Sodium Tetraphenylborates at Room and Low T ...
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Boron
Boron is a chemical element with the symbol B and atomic number 5. In its crystalline form it is a brittle, dark, lustrous metalloid; in its amorphous form it is a brown powder. As the lightest element of the '' boron group'' it has three valence electrons for forming covalent bonds, resulting in many compounds such as boric acid, the mineral sodium borate, and the ultra-hard crystals of boron carbide and boron nitride. Boron is synthesized entirely by cosmic ray spallation and supernovae and not by stellar nucleosynthesis, so it is a low-abundance element in the Solar System and in the Earth's crust. It constitutes about 0.001 percent by weight of Earth's crust. It is concentrated on Earth by the water-solubility of its more common naturally occurring compounds, the borate minerals. These are mined industrially as evaporites, such as borax and kernite. The largest known deposits are in Turkey, the largest producer of boron minerals. Elemental boron is a meta ...
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Uncoupler
An uncoupler or uncoupling agent is a molecule that disrupts oxidative phosphorylation in prokaryotes and mitochondria or photophosphorylation in chloroplasts and cyanobacteria by dissociating the reactions of ATP synthesis from the electron transport chain. The result is that the cell or mitochondrion expends energy to generate a proton-motive force, but the proton-motive force is dissipated before the ATP synthase can recapture this energy and use it to make ATP. Uncouplers are capable of transporting protons through mitochondrial and lipid membranes. Description Classical uncouplers have five properties: # the complete release of respiratory control # the substitution of all coupled processes (ATP synthesis, transhydrogenation, reverse electron flow, active transport of cations, etc.) by a cyclic proton transport mediated by the uncoupler # the elimination of all protonic and cationic gradients generated across the mitochondrial or prokaryotic membrane # no discrimination ...
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Triphenylborane
Triphenylborane, often abbreviated to BPh3 where Ph is the phenyl group C6H5-, is a chemical compound with the formula B(C6H5)3. It is a white crystalline solid and is both air and moisture sensitive, slowly forming benzene and triphenylboroxine. It is soluble in aromatic solvents. Structure and properties The core of the compound, BC3, has a trigonal planar structure. The phenyl groups are rotated at about a 30° angle from the core plane. Even though triphenylborane and tris(pentafluorophenyl)borane are structurally similar, their Lewis acidity is not. BPh3 is a weak Lewis acid while B(C6F5)3 is a strong Lewis acid due to the electronegativity of the fluorine atoms. Other boron Lewis acids include BF3 and BCl3. Synthesis Triphenylborane was first synthesized in 1922. It is typically made with boron trifluoride diethyl etherate and the Grignard reagent, phenylmagnesium bromide. : BF3•O(C2H5)2 + 3 C6H5MgBr → B(C6H5)3 + 3 MgBrF + (C2H5)2O Triphenylborane can al ...
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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 Committe ...
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Organoboron Chemistry
Organoborane or organoboron compounds are chemical compounds of boron and carbon that are organic derivatives of BH3, for example trialkyl boranes. Organoboron chemistry or organoborane chemistry is the chemistry of these compounds. Organoboron compounds are important reagents in organic chemistry enabling many chemical transformations, the most important one called hydroboration. Reactions of organoborates and boranes involve the transfer of a nucleophilic group attached to boron to an electrophilic center either inter- or intramolecularly. α,β-Unsaturated borates, as well as borates with a leaving group at the α position, are highly susceptible to intramolecular 1,2-migration of a group from boron to the electrophilic α position. Oxidation or protonolysis of the resulting organoboranes may generate a variety of organic products, including alcohols, carbonyl compounds, alkenes, and halides. Properties of the B-C bond The C-B bond has low polarity (the difference in electro ...
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Anion
An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convention. The net charge of an ion is not zero because its total number of electrons is unequal to its total number of protons. A cation is a positively charged ion with fewer electrons than protons while an anion is a negatively charged ion with more electrons than protons. Opposite electric charges are pulled towards one another by electrostatic force, so cations and anions attract each other and readily form ionic compounds. Ions consisting of only a single atom are termed atomic or monatomic ions, while two or more atoms form molecular ions or polyatomic ions. In the case of physical ionization in a fluid (gas or liquid), "ion pairs" are created by spontaneous molecule collisions, where each generated pair consists of a free electron ...
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Phenyl Group
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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Oxidative Phosphorylation
Oxidative phosphorylation (UK , US ) or electron transport-linked phosphorylation or terminal oxidation is the metabolic pathway in which cells use enzymes to oxidize nutrients, thereby releasing chemical energy in order to produce adenosine triphosphate (ATP). In eukaryotes, this takes place inside mitochondria. Almost all aerobic organisms carry out oxidative phosphorylation. This pathway is so pervasive because it releases more energy than alternative fermentation processes such as anaerobic glycolysis. The energy stored in the chemical bonds of glucose is released by the cell in the citric acid cycle producing carbon dioxide, and the energetic electron donors NADH and FADH. Oxidative phosphorylation uses these molecules and O2 to produce ATP, which is used throughout the cell whenever energy is needed. During oxidative phosphorylation, electrons are transferred from the electron donors to a series of electron acceptors in a series of redox reactions ending in oxyg ...
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Tetrakis(3,5-bis(trifluoromethyl)phenyl)borate
Tetrakis ,5-bis(trifluoromethyl)phenylorate is an anion with chemical formula 4B.html" ;"title="sub>4B">sub>4Bsup>−, which is commonly abbreviated as ArF4sup>−, indicating the presence of fluorinated aryl (ArF) groups. It is sometimes referred to as ''Kobayashi's anion'' in honour of Hiroshi Kobayashi who led the team that first synthesised it. More commonly it is affectionately nicknamed "BARF." The BARF ion is also abbreviated BArF24−, to distinguish it from the closely related , C6F5)4Bsup>−. BARF has a tetrahedral geometry around the central boron atom but each of the four surrounding aryl groups is aromatic and planar. The motivation for its preparation was the search for an anion that coordinates more weakly than the then-available ions hexafluorophosphate, tetrafluoroborate, or perchlorate. Salts of this anion are known as solids and in both aqueous and non-aqueous solutions. BARF can be used in catalytic systems where the active site requires an anion which ...
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Non-coordinating Anions
Anions that interact weakly with cations are termed non-coordinating anions, although a more accurate term is weakly coordinating anion. Non-coordinating anions are useful in studying the reactivity of electrophilic cations. They are commonly found as counterions for cationic metal complexes with an unsaturated coordination sphere. These special anions are essential components of homogeneous alkene polymerisation catalysts, where the active catalyst is a coordinatively unsaturated, cationic transition metal complex. For example, they are employed as counterions for the 14 valence electron cations C5H5)2ZrRsup>+ (R = methyl or a growing polyethylene chain). Complexes derived from non-coordinating anions have been used to catalyze hydrogenation, hydrosilylation, oligomerization, and the living polymerization of alkenes. The popularization of non-coordinating anions has contributed to increased understanding of agostic complexes wherein hydrocarbons and hydrogen serve as ligands ...
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