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Tetrabutylammonium Hydroxide
Tetrabutylammonium hydroxide is a chemical compound with the formula (C4H9)4NOH, abbreviated Bu4NOH with the acronym TBAOH or TBAH. This species is employed as a solution in water or alcohols. It is a common base in organic chemistry. Relative to more conventional inorganic bases, such as KOH and NaOH, Bu4NOH is more soluble in organic solvents.. Preparation and reactions Solutions of Bu4NOH are usually prepared ''in situ'' from butylammonium halides, Bu4NX. For example, by reacting them with silver oxide or using an ion exchange resin. Attempts to isolate Bu4NOH induces Hofmann elimination, leading to Bu3N and 1-butene. Solutions of Bu4NOH are typically contaminated with Bu3N for this reason. Treatment of Bu4NOH with a wide range of acids forms water and other tetrabutylammonium salts: : Applications Bu4NOH is a strong base that is often used under phase-transfer conditions to effect alkylations and deprotonations. Typical reactions include benzylation of amines and generati ...
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Chemical Compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element is therefore not a compound. A compound can be transformed into a different substance by a chemical reaction, which may involve interactions with other substances. In this process, bonds between atoms may be broken or new bonds formed or both. There are four major types of compounds, distinguished by how the constituent atoms are bonded together. Molecular compounds are held together by covalent bonds; ionic compounds are held together by ionic bonds; intermetallic compounds are held together by metallic bonds; coordination complexes are held together by coordinate covalent bonds. Non-stoichiometric compounds form a disputed marginal case. A chemical formula specifies the number of atoms of each element in a compound molecule, usin ...
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Deprotonation
Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H+) from a Brønsted–Lowry acid in an acid–base reaction.Henry Jakubowski, Biochemistry Online Chapter 2A3, https://employees.csbsju.edu/hjakubowski/classes/ch331/protstructure/PS_2A3_AA_Charges.html, accessed 12/2/2020 The species formed is the conjugate base of that acid. The complementary process, when a proton is added (transferred) to a Brønsted–Lowry base, is protonation (or hydronation). The species formed is the conjugate acid of that base. A species that can either accept or donate a proton is referred to as amphiprotic. An example is the H2O (water) molecule, which can gain a proton to form the hydronium ion, H3O+, or lose a proton, leaving the hydroxide ion, OH−. The relative ability of a molecule to give up a proton is measured by its p''K''a value. A low p''K''a value indicates that the compound is acidic and will easily give up its proton to a base ...
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Desilylation
Silylation is the introduction of one or more (usually) substituted silyl groups (R3Si) to a molecule. Silylations are core methods for production of organosilicon chemistry. Silanization, while similar to silylation, usually refers to attachment of silyl groups to solids. Silyl groups are commonly used for: alcohol protection, enolate trapping, gas chromatography, electron-impact mass spectrometry (EI-MS), and coordinating with metal complexes. Protection Chemistry Protection Silylation is often used to protect alcohols, as well as amines, carboxylic acids, and terminal alkynes. The products after silylation, namely silyl ethers and silyl amines, are resilient toward basic conditions. Protection is typically done by reacting the functional group with a silyl halide by an SN2 reaction mechanism, typically in the presence of base. The protection mechanism begins with the base deprotonating the alcohol group. Next, the deprotonated alcohol group attacks the silyl atom of the ...
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Tetra-n-butylammonium 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 Dissociation constant, 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. Inste ...
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Hydrofluoric Acid
Hydrofluoric acid is a solution of hydrogen fluoride (HF) in water. Solutions of HF are colorless, acidic and highly corrosive. A common concentration is 49% (48–52%) but there are also stronger solutions (e.g. 70%) and pure HF has a boiling point near room temperature. It is used to make most organofluorine compounds; examples include the commonly used pharmaceutical antidepressant medication fluoxetine (Prozac) and the material PTFE (Teflon). Elemental fluorine is produced from it. It is commonly used to etch glass and silicon wafers. Uses Production of organofluorine compounds The principal use of hydrofluoric acid is in organofluorine chemistry. Many organofluorine compounds are prepared using HF as the fluorine source, including Teflon, fluoropolymers, fluorocarbons, and refrigerants such as freon. Many pharmaceuticals contain fluorine. Production of inorganic fluorides Most high-volume inorganic fluoride compounds are prepared from hydrofluoric acid. Foremost ...
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Disodium Pyrophosphate
Disodium pyrophosphate or sodium acid pyrophosphate (SAPP) is an inorganic compound with the chemical formula . It consists of sodium cations () and dihydrogen pyrophosphate anions (). It is a white, water-soluble solid that serves as a buffering and chelating agent, with many applications in the food industry. When crystallized from water, it forms a hexahydrate, but it dehydrates above room temperature. Pyrophosphate is a polyvalent anion with a high affinity for polyvalent cations, e.g. . Disodium pyrophosphate is produced by heating sodium dihydrogen phosphate: : Food uses Disodium pyrophosphate is a popular leavening agent found in baking powders. It combines with sodium bicarbonate to release carbon dioxide: : It is available in a variety of grades that affect the speed of its action. Because the resulting phosphate residue has an off-taste, SAPP is usually used in very sweet cakes which mask the off-taste. Disodium pyrophosphate and other sodium and potassium polypho ...
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Conjugate Base
A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid gives a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as it loses a hydrogen ion in the reverse reaction. On the other hand, a conjugate base is what remains after an acid has donated a proton during a chemical reaction. Hence, a conjugate base is a substance formed by the removal of a proton from an acid, as it can gain a hydrogen ion in the reverse reaction. Because some acids can give multiple protons, the conjugate base of an acid may itself be acidic. In summary, this can be represented as the following chemical reaction: \text + \text \; \ce \; \text + \text Johannes Nicolaus Brønsted and Martin Lowry introduced the Brønsted–Lowry theory, which said that any compound that can give a proton to another compound is an acid, and the compound that receives the proton is a base. A proton is a subatomic particle in the ...
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Mineral Acid
A mineral acid (or inorganic acid) is an acid derived from one or more inorganic compounds, as opposed to organic acids which are acidic, organic compounds. All mineral acids form hydrogen ions and the conjugate base when dissolved in water. Characteristics Commonly used mineral acids are sulfuric acid (H2SO4), hydrochloric acid (HCl) and nitric acid (HNO3); these are also known as bench acids. Mineral acids range from superacids (such as perchloric acid) to very weak ones (such as boric acid). Mineral acids tend to be very soluble in water and insoluble in organic solvents. Mineral acids are used in many sectors of the chemical industry as feedstocks for the synthesis of other chemicals, both organic and inorganic. Large quantities of these acids—especially sulfuric acid, nitric acid, and hydrochloric acid—are manufactured for commercial use in large plants. Mineral acids are also used directly for their corrosive properties. For example, a dilute solution of hydrochl ...
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Neutralization (chemistry)
In chemistry, neutralization or neutralisation (see American and British English spelling differences, spelling differences) is a chemical reaction in which acid and a base (chemistry), base react with an equivalent quantity of each other. In a reaction in water, neutralization results in there being no excess of hydrogen or hydroxide ions present in the solution. The pH of the neutralized solution depends on the acid strength of the reactants. Meaning of "neutralization" In the context of a chemical reaction the term neutralization is used for a reaction between an acid and a base (chemistry), base or alkali. Historically, this reaction was represented as :acid + base (alkali) → salt + water : For example: :HCl + NaOH → NaCl + H2O The statement is still valid as long as it is understood that in an aqueous solution the substances involved are subject to dissociated, dissociation, which changes the ionization state of the substances. The arrow sign, →, is used because ...
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Chloroform
Chloroform, or trichloromethane (often abbreviated as TCM), is an organochloride with the formula and a common solvent. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to refrigerants and polytetrafluoroethylene (PTFE). Chloroform was once used as an inhalational anesthetic between the 19th century and the first half of the 20th century. It is miscible with many solvents but it is only very slightly soluble in water (only 8 g/L at 20°C). Structure and name The molecule adopts a tetrahedral molecular geometry with C3v symmetry. The chloroform molecule can be viewed as a methane molecule with three hydrogen atoms replaced with three chlorine atoms, leaving a single hydrogen atom. The name "chloroform" is a portmanteau of ''terchloride'' (tertiary chloride, a trichloride) and ''formyle'', an obsolete name for the methylylidene radical (CH) derived from formic acid. Natural occurrence Many kinds of seaweed produce chlor ...
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Dichlorocarbene
Dichlorocarbene is the reactive intermediate with chemical formula CCl2. Although this chemical species has not been isolated, it is a common intermediate in organic chemistry, being generated from chloroform. This bent diamagnetic molecule rapidly inserts into other bonds. Preparation Dichlorocarbene is most commonly generated by reaction of chloroform and a base such as potassium tert-butoxide, potassium ''tert''-butoxide or aqueous sodium hydroxide. A phase transfer catalyst, for instance quaternary ammonium cation, benzyltriethylammonium bromide, facilitates the migration of the hydroxide in the organic phase. :HCCl3 + NaOH → CCl2 + NaCl + H2O Other reagents and routes Another precursor to dichlorocarbene is ethyl trichloroacetate. Upon treatment with sodium methoxide it releases CCl2. Phenyl(trichloromethyl)mercury decomposes thermally to release CCl2. :PhHgCCl3 → CCl2 + PhHgCl Dichlorodiazirine, which is stable in the dark, chemical decomposition, decomposes into dic ...
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Benzyl
In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure . Benzyl features a benzene ring () attached to a methylene group (). Nomenclature In IUPAC nomenclature, the prefix benzyl refers to a substituent, for example benzyl chloride or benzyl benzoate. Benzyl is not to be confused with phenyl with the formula . The term benzylic is used to describe the position of the first carbon bonded to a benzene or other aromatic ring. For example, is referred to as a "benzylic" carbocation. The benzyl free radical has the formula . The benzyl cation or phenylcarbenium ion is the carbocation with formula ; the benzyl anion or phenylmethanide ion is the carbanion with the formula . None of these species can be formed in significant amounts in the solution phase under normal conditions, but they are useful referents for discussion of reaction mechanisms and may exist as reactive intermediates. Abbreviations Benzyl is most commonly abbreviated Bn. F ...
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