Lewis acid in the context of Adduct


Lewis acid in the context of Adduct

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⭐ Core Definition: Lewis acid

A Lewis acid 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 [(CH3)3B] 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.

Lewis acids and bases are named for the American physical chemist Gilbert N. Lewis.

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👉 Lewis acid in the context of Adduct

In chemistry, an adduct (from Latin adductus 'drawn toward'; alternatively, a contraction of "addition product") is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all components. The resultant is considered a distinct molecular species. Examples include the addition of sodium bisulfite to an aldehyde to give a sulfonate. It can be considered as a single product resulting from the direct combination of different molecules which comprises all atoms of the reactant molecules.

Adducts often form between Lewis acids and Lewis bases. A good example is the formation of adducts between the Lewis acid borane and the oxygen atom in the Lewis bases, tetrahydrofuran (THF): BH3·O(CH2)4 or diethyl ether: BH3·O(CH3CH2)2. Many Lewis acids and Lewis bases reacting in the gas phase or in non-aqueous solvents to form adducts have been examined in the ECW model. Trimethylborane, trimethyltin chloride and bis(hexafluoroacetylacetonato)copper(II) are examples of Lewis acids that form adducts which exhibit steric effects. For example: trimethyltin chloride, when reacting with diethyl ether, exhibits steric repulsion between the methyl groups on the tin and the ethyl groups on oxygen. But when the Lewis base is tetrahydrofuran, steric repulsion is reduced. The ECW model can provide a measure of these steric effects.

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Lewis acid in the context of Acid

An acid is a molecule or ion capable of either donating a proton (i.e. hydrogen cation, H), known as a Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid.

The first category of acids are the proton donors, or Brønsted–Lowry acids. In the special case of aqueous solutions, proton donors form the hydronium ion H3O and are known as Arrhenius acids. Brønsted and Lowry generalized the Arrhenius theory to include non-aqueous solvents. A Brønsted–Lowry or Arrhenius acid usually contains a hydrogen atom bonded to a chemical structure that is still energetically favorable after loss of H.

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Lewis acid in the context of Iron(III) chloride

Iron(III) chloride describes the inorganic compounds with the formula FeCl3(H2O)x. Also called ferric chloride, these compounds are some of the most important and commonplace compounds of iron. They are available both in anhydrous and in hydrated forms, which are both hygroscopic. They feature iron in its +3 oxidation state. The anhydrous derivative is a Lewis acid, while all forms are mild oxidizing agents. It is used as a water cleaner and as an etchant for metals.

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Lewis acid in the context of Electrophile

In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons.

Electrophiles mainly interact with nucleophiles through addition and substitution reactions. Frequently seen electrophiles in organic syntheses include cations such as H and NO, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl2 and Br2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH3 and DIBAL.

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Lewis acid in the context of Electron-donating group

Electron-rich is jargon that is used in multiple related meanings with either or both kinetic and thermodynamic implications:

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Lewis acid in the context of Superacid

In chemistry, a superacid (according to the original definition) is an acid with an acidity greater than that of 100% pure sulfuric acid (H2SO4), which has a Hammett acidity function (H0) of −12. According to the modern definition, a superacid is a medium in which the chemical potential of the proton is higher than in pure sulfuric acid. Commercially available superacids include trifluoromethanesulfonic acid (CF3SO3H), also known as triflic acid, and fluorosulfuric acid (HSO3F), both of which are about a thousand times stronger (i.e. have more negative H0 values) than sulfuric acid. Most strong superacids are prepared by the combination of a strong Lewis acid and a strong Brønsted acid. A strong superacid of this kind is fluoroantimonic acid. Another group of superacids, the carborane acid group, contains some of the strongest known acids. Finally, when treated with anhydrous acid, zeolites (microporous aluminosilicate minerals) will contain superacidic sites within their pores. These materials are used on massive scale by the petrochemical industry in the upgrading of hydrocarbons to make fuels.

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Lewis acid in the context of Acid catalysis

In acid catalysis and base catalysis, a chemical reaction is catalyzed by an acid or a base. By Brønsted–Lowry acid–base theory, the acid is the proton (hydrogen ion, H) donor and the base is the proton acceptor. Typical reactions catalyzed by proton transfer are esterifications and aldol reactions. In these reactions, the conjugate acid of the carbonyl group is a better electrophile than the neutral carbonyl group itself. Depending on the chemical species that act as the acid or base, catalytic mechanisms can be classified as either specific catalysis and general catalysis. Many enzymes operate by general catalysis.

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