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Protonation vs. Deprotonation: What's the Difference?

Edited by Huma Saeed || By Sumera Saeed || Updated on October 23, 2023
Protonation is the addition of a proton (H⁺) to a molecule; deprotonation is the removal of a proton (H⁺) from a molecule.

Key Differences

Protonation refers to the process by which an atom or molecule gains a proton (H⁺) and thereby increases its positive charge. This process results in the formation of a more positively charged species. Deprotonation, on the other hand, is the opposite process where a proton is removed from an atom or molecule, leading to a decrease in its positive charge or an increase in its negative charge.
Sumera Saeed
Oct 23, 2023
In protonation, the molecule or atom accepting the proton typically has a lone pair of electrons or a negative charge, allowing it to interact with and bind the H⁺ ion. Deprotonation, conversely, involves an atom or molecule that has at least one removable proton; this proton is then donated to another species, often a base.
Sumera Saeed
Oct 23, 2023
Considering acids and bases, protonation is usually associated with the action of a base. A base accepts a proton and becomes protonated. Deprotonation, on the other hand, is typically associated with the action of an acid. When an acid donates a proton, it undergoes deprotonation.
Sumera Saeed
Oct 23, 2023
From an energy perspective, protonation typically requires energy input, as it involves the addition of a charged species to another molecule. In contrast, deprotonation often releases energy, as it involves the removal of a charged species, leading to a more stable product.
Sumera Saeed
Oct 23, 2023

Comparison Chart

Definition

The addition of a proton (H⁺) to a molecule.
The removal of a proton (H⁺) from a molecule.
Sumera Saeed
Oct 23, 2023
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Resultant Charge

Increases the positive charge or neutralizes a negative charge.
Decreases the positive charge or makes a molecule more negative.
Sumera Saeed
Oct 23, 2023

Associated Action

Typically with a base accepting a proton.
Usually with an acid donating a proton.
Sumera Saeed
Oct 23, 2023

Energy Dynamics

Often requires energy input.
Typically releases energy.
Janet White
Oct 23, 2023

Relation with pH

Raises pH when a base is protonated.
Lowers pH when an acid is deprotonated.
Janet White
Oct 23, 2023

Protonation and Deprotonation Definitions

Protonation

The addition of a hydrogen ion to a molecule.
The nitrogen in amines undergoes protonation under acidic conditions.
Janet White
Oct 23, 2023
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Deprotonation

The removal of a hydrogen ion from a molecule.
The hydrogen in phenols undergoes deprotonation under basic conditions.
Sara Rehman
Oct 23, 2023

Protonation

A chemical reaction resulting in an increase in positive charge.
In acidic conditions, water undergoes protonation to form hydronium ions.
Sumera Saeed
Oct 23, 2023

Deprotonation

The transformation of an acid into its conjugate base.
When water acts as an acid, its deprotonation results in the formation of OH⁻.
Aimie Carlson
Oct 23, 2023

Protonation

The process of gaining a proton (H⁺).
The ammonia molecule undergoes protonation to form ammonium.
Huma Saeed
Oct 23, 2023

Deprotonation

The process of losing a proton (H⁺).
Water undergoes deprotonation to form hydroxide ions in basic conditions.
Huma Saeed
Oct 23, 2023

Protonation

The act of a molecule or atom becoming a cation by accepting a proton.
The base, hydroxide (OH⁻), experiences protonation to form water.
Janet White
Oct 23, 2023

Deprotonation

A chemical reaction resulting in a decrease in positive charge.
Acetic acid undergoes deprotonation to form acetate ions.
Sumera Saeed
Oct 23, 2023

Protonation

The transformation of a base into its conjugate acid.
When water acts as a base, its protonation results in the formation of H₃O⁺.
Janet White
Oct 23, 2023

Deprotonation

The act of a molecule or atom becoming an anion by releasing a proton.
The acid, hydronium (H₃O⁺), undergoes deprotonation to release a water molecule.
Sara Rehman
Oct 23, 2023

Protonation

(chemistry) The addition of a proton (hydrogen ion) to an atom, molecule or ion, normally to generate a cation. Category:en:Hydrogen
Sumera Saeed
Oct 14, 2019

Deprotonation

(chemistry) The removal of a proton (hydrogen ion) from a molecule to form a conjugate base.
Sumera Saeed
Oct 14, 2019

FAQs

What is protonation?

Protonation is the addition of a proton (H⁺) to a molecule.
Sumera Saeed
Oct 23, 2023

What is deprotonation?

Deprotonation is the removal of a proton (H⁺) from a molecule.
Huma Saeed
Oct 23, 2023

Which molecule undergoes protonation, an acid or a base?

A base typically undergoes protonation when it accepts a proton.
Sumera Saeed
Oct 23, 2023

How does deprotonation impact pH?

Deprotonation typically lowers pH when an acid is deprotonated.
Sumera Saeed
Oct 23, 2023

What happens to a molecule's charge during deprotonation?

During deprotonation, a molecule's positive charge decreases or it becomes more negative.
Janet White
Oct 23, 2023

How does protonation affect molecular stability?

Protonation can stabilize some molecules but destabilize others, depending on the context.
Aimie Carlson
Oct 23, 2023

How is deprotonation related to acidity?

Acids tend to undergo deprotonation, donating a proton to another species.
Aimie Carlson
Oct 23, 2023

Do protonation and deprotonation always occur in pairs?

In a given reaction, when one species undergoes protonation, another typically undergoes deprotonation.
Sara Rehman
Oct 23, 2023

Is protonation an endothermic or exothermic process?

Protonation typically requires energy input, making it often endothermic.
Sumera Saeed
Oct 23, 2023

Which molecule undergoes deprotonation, an acid or a base?

An acid typically undergoes deprotonation when it donates a proton.
Janet White
Oct 23, 2023

What results from the protonation of ammonia?

The protonation of ammonia results in the formation of ammonium ion (NH₄⁺).
Harlon Moss
Oct 23, 2023

Which molecule results from the deprotonation of water?

Deprotonation of water yields the hydroxide ion (OH⁻).
Aimie Carlson
Oct 23, 2023

Is protonation a reversible process?

Yes, protonation can be reversed through deprotonation under suitable conditions.
Sumera Saeed
Oct 23, 2023

Is the product of deprotonation always an anion?

Often, but not always. The product may be neutral or an anion depending on the initial species.
Aimie Carlson
Oct 23, 2023

Can protonation change a molecule's reactivity?

Yes, protonation can enhance or diminish a molecule's reactivity, depending on the system.
Harlon Moss
Oct 23, 2023

Which is more common in basic environments, protonation or deprotonation?

In basic environments, deprotonation is more prevalent as bases accept protons.
Sara Rehman
Oct 23, 2023

Can all molecules undergo protonation?

No, only molecules with lone pairs or negative charges typically undergo protonation.
Aimie Carlson
Oct 23, 2023

How does protonation affect pH?

Protonation often raises pH when a base is protonated.
Harlon Moss
Oct 23, 2023

Are protonation and deprotonation opposite processes?

Yes, protonation is the addition of a proton, while deprotonation is the removal of a proton.
Sara Rehman
Oct 23, 2023

Can a molecule undergo both protonation and deprotonation?

Yes, depending on the conditions, a molecule like water can both accept and donate a proton.
Sumera Saeed
Oct 23, 2023
About Author
Written by
Sumera Saeed
Sumera is an experienced content writer and editor with a niche in comparative analysis. At Diffeence Wiki, she crafts clear and unbiased comparisons to guide readers in making informed decisions. With a dedication to thorough research and quality, Sumera's work stands out in the digital realm. Off the clock, she enjoys reading and exploring diverse cultures.
Edited by
Huma Saeed
Huma is a renowned researcher acclaimed for her innovative work in Difference Wiki. Her dedication has led to key breakthroughs, establishing her prominence in academia. Her contributions continually inspire and guide her field.

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