Tetrabutylammonium Salts
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Tetrabutylammonium Salts
Tetrabutylammonium is a quaternary ammonium cation with the formula (C4H9)4sup>+. It is used in the research laboratory to prepare lipophilic salts of inorganic anions. Relative to tetraethylammonium derivatives, tetrabutylammonium salts are more lipophilic but crystallize less readily. Derivatives Some tetrabutylammonium salts of simple anions include: *tetrabutylammonium fluoride, a desilylation reagent. *tetrabutylammonium bromide, a precursor to other tetrabutylammonium salts via salt metathesis reactions. *tetrabutylammonium iodide, a low cost catalyst. *tetrabutylammonium triiodide, a common carrier of the triiodide anion used in chemical synthesis. *tetrabutylammonium hydroxide, a precursor to other tetrabutylammonium salts via acid-base reactions. *tetrabutylammonium hexafluorophosphate, an electrolyte for nonaqueous electrochemistry. Some tetrabutylammonium salts of more complex examples include: *polyoxometalates. *NS. * metal carbonyl anions. *Synthetic iron-sulfur clus ...
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Tetrabutylammonium Fluoride
Tetra-''n''-butylammonium fluoride, commonly abbreviated to TBAF and ''n''-Bu4NF, is a quaternary ammonium salt with the chemical formula (CH3CH2CH2CH2)4N+F−. It is commercially available as the white solid trihydrate and as a solution in tetrahydrofuran. TBAF is used as a source of fluoride ion in organic solvents. Preparation and properties TBAF can be prepared by passing hydrofluoric acid through an ion-exchange resin, followed by tetrabutylammonium bromide. Upon evaporation of the water, TBAF can be collected as an oil in quantitative yield. Preparing anhydrous samples is of interest as the basicity of fluoride increases by more than 20 p''K'' units on passing from aqueous to aprotic solvent. However, heating samples of the hydrated material to 77 °C under vacuum causes decomposition to the hydrogen difluoride salt. Similarly, samples dried at 40 °C under high vacuum still contain 10-30 mol% of water and some 10% of difluoride. Instead, anhydrous TBAF ha ...
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Triiodide
In chemistry, triiodide usually refers to the triiodide ion, . This anion, one of the polyhalogen ions, is composed of three iodine atoms. It is formed by combining aqueous solutions of iodide salts and iodine. Some salts of the anion have been isolated, including thallium(I) triiodide (Tl+ 3sup>−) and ammonium triiodide ( H4sup>+ 3sup>−). Triiodide is observed to be a red colour in solution. Nomenclature Other chemical compounds with "triiodide" in their name may contain three iodide centers that are not bonded to each other as the triiodide ion, but exist instead as separate iodine atoms or iodide ions. Examples include nitrogen triiodide (NI3) and phosphorus triiodide (PI3), where individual iodine atoms are covalently bonded to a central atom. As some cations have the theoretical possibility to form compounds with both triiodide and iodide ions, such as ammonium, compounds containing iodide anions in a 3:1 stoichiometric ratio should only be referred to as triiodides ...
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Quaternary Ammonium Compounds
In chemistry, quaternary ammonium cations, also known as quats, are positively charged polyatomic ions of the structure , R being an alkyl group or an aryl group. Unlike the ammonium ion () and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds (called quaternary amines in oilfield parlance) are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule. Quats are used in consumer applications including as antimicrobials (such as detergents and disinfectants), fabric softeners, and hair conditioners. As an antimicrobial, they are able to inactivate enveloped viruses (such as SARS-CoV-2). Quats tend to be gentler on surfaces than bleach-based disinfectants, and are generally fabric-safe. Synthesis Quaternary ammonium compou ...
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Reagents For Organic Chemistry
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a substance ''consumed'' in the course of a chemical reaction. ''Solvents'', though involved in the reaction mechanism, are usually not called reactants. Similarly, ''catalysts'' are not consumed by the reaction, so they are not reactants. In biochemistry, especially in connection with enzyme-catalyzed reactions, the reactants are commonly called substrates. Definitions Organic chemistry In organic chemistry, the term "reagent" denotes a chemical ingredient (a compound or mixture, typically of inorganic or small organic molecules) introduced to cause the desired transformation of an organic substance. Examples include the Collins reagent, Fenton's reagent, and Grignard reagents. Analytical chemistry In analytical chemistry, a reagent ...
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N-Butyllithium
''n''-Butyllithium C4H9Li (abbreviated ''n''-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds as in the pharmaceutical industry. Butyllithium is commercially available as solutions (15%, 25%, 1.5  M, 2 M, 2.5 M, 10 M, etc.) in alkanes such as pentane, hexanes, and heptanes. Solutions in diethyl ether and THF can be prepared, but are not stable enough for storage. Annual worldwide production and consumption of butyllithium and other organolithium compounds is estimated at 2000 to 3000 tonnes. Although butyllithium is colorless, ''n''-butyllithium is usually encountered as a pale yellow solution in alkanes. Such solutions are stable indefinitely if properly stored,. but in practice, they degrade upon aging. Fine white precipitate (l ...
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Potassium Octachlorodirhenate
Potassium octachlorodirhenate(III) is an inorganic compound with the formula K2 Re2 Cl8. This dark blue salt is well known as an early example of a compound featuring quadruple bond between its metal centers. Although the compound has no practical value, its characterization was significant in opening a new field of research into complexes with quadruple bonds. Synthesis and reactions Soviet chemists first reported K2 e2Cl8in 1954, but it was not until 1964 that Cotton and Harris characterized the compound as featuring a short Re–Re bond, the first of its kind discovered. The results of this classic study subsequently led to new work into other metals capable of forming metal–metal bonds, such as chromium, molybdenum, tungsten, and technetium. A high-yield synthesis of the tetrabutylammonium salt involves treating the perrhenate salt with benzoyl chloride followed by HCl: :2  ''n''-C4H9)4N">n-Butyl">''n''-C4H9)4N ReO4 + 8  C6H5COCl → ''n''-C4H9)4Nsub>2 e2Cl8+ ...
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Iron-sulfur Cluster
Iron–sulfur proteins (or iron–sulphur proteins in British spelling) are proteins characterized by the presence of iron–sulfur clusters containing sulfide-linked di-, tri-, and tetrairon centers in variable oxidation states. Iron–sulfur clusters are found in a variety of metalloproteins, such as the ferredoxins, as well as NADH dehydrogenase, hydrogenases, coenzyme Q – cytochrome c reductase, succinate – coenzyme Q reductase and nitrogenase. Iron–sulfur clusters are best known for their role in the oxidation-reduction reactions of electron transport in mitochondria and chloroplasts. Both Complex I and Complex II of oxidative phosphorylation have multiple Fe–S clusters. They have many other functions including catalysis as illustrated by aconitase, generation of radicals as illustrated by SAM-dependent enzymes, and as sulfur donors in the biosynthesis of lipoic acid and biotin. Additionally, some Fe–S proteins regulate gene expression. Fe–S proteins are ...
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Metal Carbonyl Cluster
In chemistry, a metal carbonyl cluster is a compound that contains two or more metals linked in part by metal-metal bonds and containing carbon monoxide (CO) as the exclusive or predominant ligand. The area is a subfield of metal carbonyl chemistry, and many metal carbonyl clusters are in fact prepared from simple metal carbonyls. Simple examples include Fe2(CO)9, Fe3(CO)12, Mn2(CO)10. High nuclearity clusters include h13(CO)24H3sup>2− and the stacked Pt3 triangules t3n(CO)6nsup>2− (n = 2–6). History The first metal carbonyl clusters, Fe3(CO)12, Ir4(CO)12, and Rh6(CO)16, were reported starting in the 1930s, often by Walter Hieber. The structures were subsequently established by X-ray crystallography.. Paolo Chini (1928–1980) was a pioneer for the synthesis and characterization of high nuclearity metal carbonyl clusters. His first studies started in 1958, in the attempt to repeat a patent that claimed an improved selectivity in hydroformylation. From a mixture of ...
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Polyoxometalate
In chemistry, a polyoxometalate (abbreviated POM) is a polyatomic ion, usually an anion, that consists of three or more transition metal oxyanions linked together by shared oxygen atoms to form closed 3-dimensional frameworks. The metal atoms are usually group 6 (Mo, W) or less commonly group 5 ( V, Nb, Ta) transition metals and Tc in their high oxidation states. Polyoxometalates are often colorless, orange or red diamagnetic anions. Two broad families are recognized, isopolymetalates, composed of only one kind of metal and oxide, and heteropolymetalates, composed of one metal, oxide, and a main group oxyanion (phosphate, silicate, etc.). Many exceptions to these general statements exist. Formation The oxides of d0 metals such as , , dissolve at high pH to give orthometalates, , , . For and , the nature of the dissolved species at high pH is less clear, but these oxides also form polyoxometalates. As the pH is lowered, orthometalates protonate to give oxide–hydroxide comp ...
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Tetrabutylammonium Triiodide
Tetra-''n''-butylammonium triiodide (TBAI3) is a quaternary ammonium salt with a triiodide counterion. It is a common carrier of the triiodide used in chemical synthesis of photovoltaic materials, organic conductors and superconductors. In crystals, the triiodide moieties are linear and shows high crystallinity.{{Cite journal , last1=Brotherton , first1=Wendy S. , last2=Clark , first2=Ronald J. , last3=Zhu , first3=Lei , date=2012-08-03 , title=Synthesis of 5-Iodo-1,4-disubstituted-1,2,3-triazoles Mediated by in Situ Generated Copper(I) Catalyst and Electrophilic Triiodide Ion , url=https://doi.org/10.1021/jo300841c , journal=The Journal of Organic Chemistry , volume=77 , issue=15 , pages=6443–6455 , doi=10.1021/jo300841c , pmid=22780866 , issn=0022-3263 The crystals have a black appearance with a needle or plate-like habit. See also * Triiodide * Tetrabutylammonium tribromide * Organic superconductor An organic superconductor is a synthetic organic compound that exhibits s ...
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Tetrabutylammonium Bromide
Tetrabutylammonium bromide (TBAB) is a quaternary ammonium salt with a bromide commonly used as a phase transfer catalyst. It is used to prepare many other tetrabutylammonium salts by salt metathesis reactions. The anhydrous form is a white solid. In addition to being cheap, tetrabutylammonium bromide is also environmentally friendly, has a greater degree of selectivity, is operationally simple, non-corrosive, and can be recycled easily as well. Preparation and reactions Tetrabutylammonium bromide can be prepared by the alkylation of tributylamine with 1-bromobutane. Tetrabutylammonium bromide is used to prepare other salts of the tetrabutylammonium cation by salt metathesis reactions., , ;. It serves as a source of bromide ions for substitution reactions. It is one of a commonly-used phase transfer catalyst. As its melting point is just over 100 °C and decreases in the presence of other reagents, it can be considered an ionic liquid. Role in semi-clathrate formation TBAB ...
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Tetra-n-butylammonium Iodide
Tetra-''n''-butylammonium iodide (TBAI) is a quaternary ammonium salt with an iodide counterion. It is used for synthesizing tetra-''n''-butylammonium triiodide by mixing with iodine. Properties The solid crystal of tetra-''n''-butylammonium iodide is in the monoclinic crystal system. It has space group ''C''2/''c''. The unit cell has dimensions a=14.2806 b=14.1864 c=19.5951 β=111.149. There are eight formulae in the unit cell (Z=8), which has volume 3702.4 Å3. The enthalpy of formation ΔfH0 of tetra-''n''-butylammonium iodide is −499 kJ/mol, which is lower than that for the bromide or chloride (−540, −564 kJ/mol). At lower temperatures with water tetra-''n''-butylammonium iodide forms a clathrate hydrate. The tetra-''n''-butylammonium cation is large and hydrophobic. The absolute enthalpy of hydration (from gas phase) is −260 kJ/mol. The He(I) photoelectron spectrum of tetra-''n''-butylammonium iodide contains a peak at 11 eV due to the te ...
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