Deprotonation

A chemical reaction involving the removal of a proton from a molecule

Deprotonation

Illustration of a deprotonation reaction

Deprotonation is a chemical reaction in which a proton (H_) is removed from a molecule, forming the conjugate base of the molecule and a hydronium ion (H_O_) in aqueous solution. This process is a fundamental concept in acid-base chemistry and is the reverse of protonation.

Mechanism

Deprotonation typically occurs when a base interacts with an acid, abstracting a proton from the acid. The strength of the base and the acidity of the proton determine the extent of deprotonation. Strong bases, such as hydroxide ions (OH_), are more effective at deprotonating weak acids.

Factors Affecting Deprotonation

Several factors influence the deprotonation process:

• Acidity of the Proton: The more acidic the proton, the easier it is to remove. Acidity is often measured by the pKa value; lower pKa values indicate stronger acids.
• Strength of the Base: Stronger bases are more capable of deprotonating acids. The pKb value is used to measure base strength.
• Solvent Effects: The solvent can stabilize or destabilize the ions formed during deprotonation, affecting the reaction's equilibrium.
• Temperature: Higher temperatures can increase the rate of deprotonation by providing the necessary energy to overcome activation barriers.

Applications

Deprotonation is a crucial step in many chemical reactions, including:

• Organic synthesis: Deprotonation is used to generate carbanions, which are key intermediates in many organic reactions.
• Biochemistry: Enzyme-catalyzed reactions often involve deprotonation steps, such as in the catalytic triad of serine proteases.
• Industrial chemistry: Deprotonation reactions are used in the production of polymers and other chemical products.

Related Concepts

• Protonation
• Acid dissociation constant
• Conjugate acid-base pair
• Brønsted-Lowry acid-base theory

Related pages

• Acid-base reaction
• pH
• Buffer solution