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TASF Reagent
The TASF reagent or tris(dimethylamino)sulfonium difluorotrimethylsilicate is a reagent in organic chemistry with structural formula (CH3)2N)3Ssup>+ 2Si(CH3)3sup>−. It is an anhydrous source of fluoride and is used to cleave silyl ether protective groups. Many other fluoride reagents are known, but few are truly anhydrous, because of the extraordinary basicity of "naked" F−. In TASF, the fluoride is masked as an adduct with the weak Lewis acid trimethylsilylfluoride (FSi(CH3)3). The sulfonium cation ((CH3)2N)3S+ is unusually non-electrophilic due to the electron-donating properties of the three (CH3)2N substituents. This compound is prepared from sulfur tetrafluoride: :3 (CH3)2NSi(CH3)3 + SF4 → 2 (CH3)3SiF + (CH3)2N)3Ssup>+ 2Si(CH3)3sup>− The colorless salt precipitates from the reaction solvent, diethyl ether. Structure The cation (CH3)2N)3Ssup>+ is a sulfonium ion. The S-N distances are 1.612 and 1.675 pm. The N-S-N angles are 99.6°. The anion is 2Si(CH ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Reagent
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical ( in silico) study. The range of chemicals studied in organic chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but also containing other elements, especially oxygen, nitrogen, sulfur, phosphorus (included in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Structural Formula
The structural formula of a chemical compound is a graphic representation of the molecular structure (determined by structural chemistry methods), showing how the atoms are possibly arranged in the real three-dimensional space. The chemical bonding within the molecule is also shown, either explicitly or implicitly. Unlike other chemical formula types, which have a limited number of symbols and are capable of only limited descriptive power, structural formulas provide a more complete geometric representation of the molecular structure. For example, many chemical compounds exist in different isomeric forms, which have different enantiomeric structures but the same molecular formula. There are multiple types of ways to draw these structural formulas such as: Lewis Structures, condensed formulas, skeletal formulas, Newman projections, Cyclohexane conformations, Haworth projections, and Fischer projections. Several systematic chemical naming formats, as in chemical databases, are used ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Fluoride
Fluoride (). According to this source, is a possible pronunciation in British English. is an inorganic, monatomic anion of fluorine, with the chemical formula (also written ), whose salts are typically white or colorless. Fluoride salts typically have distinctive bitter tastes, and are odorless. Its salts and minerals are important chemical reagents and industrial chemicals, mainly used in the production of hydrogen fluoride for fluorocarbons. Fluoride is classified as a weak base since it only partially associates in solution, but concentrated fluoride is corrosive and can attack the skin. Fluoride is the simplest fluorine anion. In terms of charge and size, the fluoride ion resembles the hydroxide ion. Fluoride ions occur on Earth in several minerals, particularly fluorite, but are present only in trace quantities in bodies of water in nature. Nomenclature Fluorides include compounds that contain ionic fluoride and those in which fluoride does not dissociate. The nom ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Silyl Ether
Silyl ethers are a group of chemical compounds which contain a silicon atom covalently bonded to an alkoxy group. The general structure is R1R2R3Si−O−R4 where R4 is an alkyl group or an aryl group. Silyl ethers are usually used as protecting groups for alcohols in organic synthesis. Since R1R2R3 can be combinations of differing groups which can be varied in order to provide a number of silyl ethers, this group of chemical compounds provides a wide spectrum of selectivity for protecting group chemistry. Common silyl ethers are: trimethylsilyl (TMS), ''tert''-butyldiphenylsilyl (TBDPS), ''tert''-butyldimethylsilyl (TBS/TBDMS) and triisopropylsilyl (TIPS). They are particularly useful because they can be installed and removed very selectively under mild conditions. Common silyl ethers Formation Commonly silylation of alcohols requires a silyl chloride and an amine base. One reliable and rapid procedure is the Corey protocol in which the alcohol is reacted with a silyl chlori ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Protective Group
A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In many preparations of delicate organic compounds, some specific parts of their molecules cannot survive the required reagents or chemical environments. Then, these parts, or groups, must be protected. For example, lithium aluminium hydride is a highly reactive but useful reagent capable of reducing esters to alcohols. It will always react with carbonyl groups, and this cannot be discouraged by any means. When a reduction of an ester is required in the presence of a carbonyl, the attack of the hydride on the carbonyl has to be prevented. For example, the carbonyl is converted into an acetal, which does not react with hydrides. The acetal is then called a protecting group for the carbonyl. After the step involving the hydride is complete, the acet ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lewis Acid
A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any species that has a filled orbital containing an electron pair which is not involved in bonding but may form a dative bond with a Lewis acid to form a Lewis adduct. For example, NH3 is a Lewis base, because it can donate its lone pair of electrons. Trimethylborane (Me3B) is a Lewis acid as it is capable of accepting a lone pair. In a Lewis adduct, the Lewis acid and base share an electron pair furnished by the Lewis base, forming a dative bond. In the context of a specific chemical reaction between NH3 and Me3B, a lone pair from NH3 will form a dative bond with the empty orbital of Me3B to form an adduct NH3•BMe3. The terminology refers to the contributions of Gilbert N. Lewis. From p. 142: "We are inclined to think of substances as po ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfonium
In organic chemistry, a sulfonium ion, also known as sulphonium ion or sulfanium ion, is a positively-charged ion (a " cation") featuring three organic substituents attached to sulfur. These organosulfur compounds have the formula . Together with a negatively-charged counterion, they give sulfonium salts. They are typically colorless solids that are soluble in organic solvent. Synthesis Sulfonium compounds are usually synthesized by the reaction of thioethers with alkyl halides. For example, the reaction of dimethyl sulfide with iodomethane yields trimethylsulfonium iodide: : + → The reaction proceeds by a nucleophilic substitution mechanism (SN2). Iodide is the leaving group departs. The rate of methylation is faster with more electrophilic methylating agents, such as methyl trifluoromethanesulfonate. Inversion Sulfonium ions with three different substituents are chiral owing to their pyramidal structure. Unlike the isoelectronic oxonium ions (R3O+), chiral sulfon ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfur Tetrafluoride
Sulfur tetrafluoride is the chemical compound with the formula S F4. It is a colorless corrosive gas that releases dangerous HF upon exposure to water or moisture. Despite these unwelcome characteristics, this compound is a useful reagent for the preparation of organofluorine compounds, some of which are important in the pharmaceutical and specialty chemical industries. Structure Sulfur in SF4 is in the formal +4 oxidation state. Of sulfur's total of six valence electrons, two form a lone pair. The structure of SF4 can therefore be anticipated using the principles of VSEPR theory: it is a see-saw shape, with S at the center. One of the three equatorial positions is occupied by a nonbonding lone pair of electrons. Consequently, the molecule has two distinct types of F ligands, two axial and two equatorial. The relevant bond distances are = 164.3 pm and = 154.2 pm. It is typical for the axial ligands in hypervalent molecules to be bonded less strongly. In c ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diethyl Ether
Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It is commonly used as a solvent in laboratories and as a starting fluid for some engines. It was formerly used as a general anesthetic, until non-flammable drugs were developed, such as halothane. It has been used as a recreational drug to cause intoxication. Production Most diethyl ether is produced as a byproduct of the vapor-phase hydration of ethylene to make ethanol. This process uses solid-supported phosphoric acid catalysts and can be adjusted to make more ether if the need arises. Vapor-phase dehydration of ethanol over some alumina catalysts can give diethyl ether yields of up to 95%. Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis. Ethanol is mixed with a stro ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfonium Ion
In organic chemistry, a sulfonium ion, also known as sulphonium ion or sulfanium ion, is a positively-charged ion (a " cation") featuring three organic substituents attached to sulfur. These organosulfur compounds have the formula . Together with a negatively-charged counterion, they give sulfonium salts. They are typically colorless solids that are soluble in organic solvent. Synthesis Sulfonium compounds are usually synthesized by the reaction of thioethers with alkyl halides. For example, the reaction of dimethyl sulfide with iodomethane yields trimethylsulfonium iodide: : + → The reaction proceeds by a nucleophilic substitution mechanism (SN2). Iodide is the leaving group departs. The rate of methylation is faster with more electrophilic methylating agents, such as methyl trifluoromethanesulfonate. Inversion Sulfonium ions with three different substituents are chiral owing to their pyramidal structure. Unlike the isoelectronic oxonium ions (R3O+), chiral sulfon ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Trigonal Bipyramid
In geometry, the triangular bipyramid (or dipyramid) is a type of hexahedron, being the first in the infinite set of face-transitive bipyramids. It is the dual of the triangular prism with 6 isosceles triangle faces. As the name suggests, it can be constructed by joining two tetrahedra along one face. Although all its faces are congruent and the solid is face-transitive, it is not a Platonic solid because some vertices adjoin three faces and others adjoin four. The bipyramid whose six faces are all equilateral triangles is one of the Johnson solids, (). As a Johnson solid with all faces equilateral triangles, it is also a deltahedron. Formulae The following formulae for the height (H), surface area (A) and volume (V) can be used if all faces are regular, with edge length L: :H = L\cdot \frac \approx L\cdot 1.632993162 :A = L^2 \cdot \frac \approx L^2\cdot 2.598076211 :V = L^3 \cdot \frac \approx L^3\cdot 0.235702260 Dual polyhedron The dual polyhedron of the ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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3S _in_the_BPh4-_salt_(code_HEYZAM).png "Click for more on -> Sulfonium")
