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Trifluoroacetic Acid
Trifluoroacetic acid (TFA) is a synthetic organofluorine compound with the chemical formula CF3CO2H. It belongs to the subclass of per- and polyfluoroalkyl substances (PFASs) known as ultrashort-chain perfluoroalkyl acids (PFAAs). TFA is not produced biologically or abiotically and is commonly used in organic chemistry for various purposes. It is the most abundant PFAS found in the environment. It is a haloacetic acid, with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms. It is a colorless liquid with a vinegar-like odor. TFA is a stronger acid than acetic acid, having an acid ionisation constant, ''K''a, that is approximately 34,000 times higher, as the highly electronegative fluorine atoms and consequent electron-withdrawing nature of the trifluoromethyl group weakens the oxygen-hydrogen bond (allowing for greater acidity) and stabilises the anionic conjugate base. Synthesis TFA is prepared industrially by the electrofluorination of ac ...
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Today's Featured Article
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Electronegative
Electronegativity, symbolized as , is the tendency for an atom of a given chemical element to attract shared electrons (or electron density) when forming a chemical bond. An atom's electronegativity is affected by both its atomic number and the distance at which its valence electrons reside from the charged nucleus. The higher the associated electronegativity, the more an atom or a substituent group attracts electrons. Electronegativity serves as a simple way to quantitatively estimate the bond energy, and the sign and magnitude of a bond's chemical polarity, which characterizes a bond along the continuous scale from covalent to ionic bonding. The loosely defined term electropositivity is the opposite of electronegativity: it characterizes an element's tendency to donate valence electrons. On the most basic level, electronegativity is determined by factors like the nuclear charge (the more protons an atom has, the more "pull" it will have on electrons) and the number and locatio ...
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Hydrazoic Acid
Hydrazoic acid, also known as hydrogen azide, azic acid or azoimide, This also contains a detailed description of the contemporaneous production process. is a compound with the chemical formula . It is a colorless, volatile, and explosive liquid at room temperature and pressure. It is a compound of nitrogen and hydrogen, and is therefore a pnictogen hydride. It was first isolated in 1890 by Theodor Curtius. The acid has few applications, but its conjugate base, the azide ion, is useful in specialized processes. Hydrazoic acid, like its fellow mineral acids, is soluble in water. Undiluted hydrazoic acid is dangerously explosive with a standard enthalpy of formation ΔfHo (l, 298K) = +264 kJ/mol. When dilute, the gas and aqueous solutions (<10%) can be safely prepared but should be used immediately; because of its low boiling point, hydrazoic acid is enriched upon evaporation and condensation such that dilute solutions incapable of explosion can form droplets in the headspace of th ...
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Hexachloropropene
Hexachloropropene is a compound of chlorine and carbon with the linear formula CCl3CCl=CCl2. It is a colourless liquid at room temperature. It is toxic for humans. Hexachloropropene can be produced by the dehydrochlorination reaction of 1,1,1,2,2,3,3-heptachloropropane by potassium hydroxide in methanol solution. 1,1,1,2,2,3,3-Heptachloropropane is produced by the reaction of chloroform and tetrachloroethylene: : : Hexachloropropene can be used to produce other compounds such as uranium tetrachloride, anhydrous niobium pentachloride and tungsten hexachloride Tungsten hexachloride is an inorganic chemical compound of tungsten and chlorine with the chemical formula . This dark violet-blue compound exists as volatile crystals under standard conditions. It is an important starting reagent in the prepar .... References {{DEFAULTSORT:Hexachloropropene Chloroalkenes Perchlorocarbons ...
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Swarts Fluorination
Swarts fluorination is a process whereby the chlorine atoms in a compound – generally an organic compound, but experiments have been performed using silanes – are replaced with fluorine, by treatment with antimony trifluoride in the presence of chlorine or of antimony pentachloride. Some metal fluorides are particularly more useful than others, including silver(I) fluoride, mercurous fluoride, cobalt(II) fluoride and aforementioned antimony. Heating the mixture of the metal fluoride and the haloalkane (chlorine and bromine are replaced readily) yields the desired fluoroalkane. In some particularly reactive cases, heating is unnecessary; shaking or stirring the reaction mixture is sufficient. This reaction has a good yield. The process was initially described by Frédéric Swarts, Frédéric Jean Edmond Swarts in 1892. Mechanism The active species is antimony trifluorodichloride 2, which is produced in situ from the reaction between antimony trifluoride 1 and chlorine; this ...
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Potassium Permanganate
Potassium permanganate is an inorganic compound with the chemical formula KMnO4. It is a purplish-black crystalline salt, which dissolves in water as K+ and ions to give an intensely pink to purple solution. Potassium permanganate is widely used in the chemical industry and laboratories as a strong oxidizing agent, and also as a medication for dermatitis, for cleaning wounds, and general disinfection. It is commonly used as a biocide for water treatment purposes. It is on the World Health Organization's List of Essential Medicines. In 2000, worldwide production was estimated at 30,000 tons. Properties Potassium permanganate is the potassium salt of the tetrahedral transition metal oxo complex permanganate, in which four ligands are bound to a manganese(VII) center. Structure forms orthorhombic crystals with constants: ''a'' = 910.5  pm, ''b'' = 572.0 pm, ''c'' = 742.5 pm. The overall motif is similar to that for barium sulfate, with which it forms solid so ...
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Redox
Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a decrease in the oxidation state. The oxidation and reduction processes occur simultaneously in the chemical reaction. There are two classes of redox reactions: * Electron transfer, Electron-transfer – Only one (usually) electron flows from the atom, ion, or molecule being oxidized to the atom, ion, or molecule that is reduced. This type of redox reaction is often discussed in terms of redox couples and electrode potentials. * Atom transfer – An atom transfers from one Substrate (chemistry), substrate to another. For example, in the rusting of iron, the oxidation state of iron atoms increases as the iron converts to an oxide, and simultaneously, the oxidation state of oxygen decreases as it accepts electrons r ...
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Trifluoroacetic Anhydride
Trifluoroacetic anhydride (TFAA) is the acid anhydride of trifluoroacetic acid. It is the perfluorinated derivative of acetic anhydride. Preparation Trifluoroacetic anhydride was originally prepared by the dehydration of trifluoroacetic acid with phosphorus pentoxide. The dehydration might also be carried out with excess α-halogenated acid chlorides. For example, with dichloroacetyl chloride: : 2 CF3COOH + Cl2CHCOCl → (CF3CO)2O + Cl2CHCOOH + HCl Uses Trifluoroacetic anhydride has various uses in organic synthesis. It may be used to introduce the corresponding trifluoroacetyl group, for which it is more convenient than the corresponding acyl chloride, trifluoroacetyl chloride, which is a gas. It can be used to promote reactions of carboxylic acids, including Friedel-Crafts acylation and acylation of other unsaturated compounds. Other electrophilic aromatic substitution reactions can also be promoted with trifluoroacetic anhydride, including nitration, sulfonation and ni ...
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Acetic Anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of cellulose acetate as well as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air. Structure and properties Acetic anhydride, like most organic acid anhydrides, is a flexible molecule with a nonplanar structure. The C=O and C-O distances are 1.19 and 1.39 Å. The Pi bond, pi system linkage through the central oxygen offers very weak resonance stabilization compared to the dipole, dipole-dipole repulsion between the two carbonyl oxygens. The energy barriers to bond rotation between each of the optimal aplanar conformations are quite low. Production Acetic anhydride was first synthesized in 1852 by the French chemist Charles Frédéric Gerhardt ...
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Acetyl Chloride
Acetyl chloride () is an acyl chloride derived from acetic acid (). It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl. Synthesis On an industrial scale, the reaction of acetic anhydride with hydrogen chloride produces a mixture of acetyl chloride and acetic acid: : Laboratory routes Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride. Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as phosphorus trichloride (), phosphorus pentachloride (), sulfuryl chloride (), phosgene, or thionyl chloride (). However, these methods usually give acetyl chloride contaminated by phosphorus or sulfur impurities, which may interfere with the organic reactions. Other methods When heated, a mixture of dichloroacetyl chloride and acetic aci ...
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Electrofluorination
Electrochemical fluorination (ECF), or electrofluorination, is a foundational organofluorine chemistry method for the preparation of fluorocarbon-based organofluorine compounds.G. Siegemund, W. Schwertfeger, A. Feiring, B. Smart, F. Behr, H. Vogel, B. McKusick "Fluorine Compounds, Organic" in "Ullmann’s Encyclopedia of Industrial Chemistry" 2005, Wiley-VCH, Weinheim. The general approach represents an application of electrosynthesis. The fluorinated chemical compounds produced by ECF are useful because of their distinctive solvation properties and the relative inertness of carbon–fluorine bonds. Two ECF synthesis routes are commercialized and commonly applied: the Simons process and the Phillips Petroleum process. It is also possible to electrofluorinate in various organic media.Fred G. Drakesmith "Electrofluorination of Organic Compounds" Topics in Current Chemistry, Vol. 193, Springer, Berlin-Heidelberg, 1997. Prior to the development of these methods, fluorination with fl ...
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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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