Deprotonation

Deprotonation is the removal of a proton (H⁺) from a chemical species. It is the reverse of protonation and commonly occurs when a base accepts the proton.

Brønsted–Lowry acid–base theory: An acid–base model in which acids donate protons and bases accept them. Deprotonation is the proton-donation half of a Brønsted–Lowry acid–base reaction.
Proton: A positively charged subatomic particle found in atomic nuclei; in chemistry, H⁺ denotes a hydrogen nucleus. Deprotonation specifically removes this particle from a chemical species.
Enolate: An anion formed by deprotonating the alpha carbon of a carbonyl compound, with charge delocalized onto oxygen. This reactive intermediate is produced by removing an alpha proton from a carbonyl compound.
Dehydrogenation: A chemical reaction that removes hydrogen atoms from a molecule, often forming a new bond or increasing unsaturation. Unlike deprotonation, it removes hydrogen in a broader redox transformation, not simply H⁺.
Acetate: The anion CH₃COO⁻, formed when acetic acid loses a proton. It is a common example of a stable conjugate base formed by deprotonation.
Conjugate acid–base pair: Two species related by the gain or loss of a proton. Removing a proton converts an acid into its conjugate base.
Acid: A substance that donates protons under the Brønsted–Lowry definition. A Brønsted–Lowry acid is the species that loses a proton during deprotonation.
Saponification: The base-promoted hydrolysis of an ester, commonly used to make soap from fats or oils. Deprotonation steps help enable the nucleophilic reactions in this base-driven process.
Homolysis: Bond cleavage in which each bonded atom retains one electron from the bond. Deprotonation is heterolytic proton loss; homolysis instead splits a bond into radicals.
Phenoxide: The anion C₆H₅O⁻, formed by removing the hydroxyl proton from phenol. It illustrates how resonance stabilizes the species left after deprotonation.

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