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Deprotonation of acetic acid by a hydroxide ion. 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. [1] [2] The species formed is the conjugate base of that acid.
Acids and bases; Acceptor number; Acid; Acid–base reaction; Acid–base homeostasis; ... This reaction (deprotonation with LDA) is commonly used to generate enolates.
Protonation and deprotonation (removal of a proton) occur in most acid–base reactions; they are the core of most acid–base reaction theories. A Brønsted–Lowry acid is defined as a chemical substance that protonates another substance.
In chemistry, an acid–base reaction is a chemical reaction that occurs between an acid and a base.It can be used to determine pH via titration.Several theoretical frameworks provide alternative conceptions of the reaction mechanisms and their application in solving related problems; these are called the acid–base theories, for example, Brønsted–Lowry acid–base theory.
The deprotonation of carbon acids can proceed with either kinetic or thermodynamic reaction control. For example, in the case of phenylacetone , deprotonation can produce two different enolates. LDA has been shown to deprotonate the methyl group, which is the kinetic course of the deprotonation.
The base is most commonly histidine since its pK a allows for effective base catalysis, hydrogen bonding to the acid residue, and deprotonation of the nucleophile residue. [1] β-lactamases such as TEM-1 use a lysine residue as the base.
The deprotonation of carbon acids can proceed with either kinetic or thermodynamic reaction control. Kinetic controlled deprotonation requires a base that is sterically hindered and strong enough to remove the proton irreversibly. For example, in the case of phenylacetone, deprotonation can produce two different enolates. LDA has been shown to ...
Strong bases are leveling solvents for acids, weak bases are differentiating solvents for acids. In a leveling solvent, many acids are completely dissociated and are thus of the same strength. All acids tend to become indistinguishable in strength when dissolved in strongly basic solvents owing to the greater affinity of strong bases for protons.