Deprotonation

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Deprotonation

Deprotonation is a chemistry

Chemistry

Chemistry is the science concerned with the composition, structure, and properties of matter, as well as the changes it undergoes during chemical reactions....
term that refers to the removal of a proton

Proton

The proton is a subatomic particle with an electric charge of +1 elementary charge. It is found in the nucleus of each atom but is also stable by itself and has a second identity as the hydrogen ion, H+....
(hydronium

Hydronium

In chemistry, hydronium is the common name for the aqueous cation hydrogen3oxygen+ derived from protonation of water. It is the simplest type of an oxonium ion....
cation H₃O⁺) from a molecule

Molecule

In chemistry, a molecule is defined as a sufficiently stable, electric charge neutral group of at least two atoms in a definite arrangement held together by very strong chemical bonds....
, forming the conjugate base. The relative ability for a molecule to give up a proton is measured by a pK_a

PKA

PKA or pKa may be:* Protein kinase A, a cAMP activated protein kinase* pKa, the symbol for Acid dissociation constant...
value. A low pK_a value indicates that the compound is acidic and will easily give up its proton to a base

Base (chemistry)

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Encyclopedia

Deprotonation is a chemistry

Chemistry

Proton

Hydronium

Molecule

PKA

Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
. The pK_a of a compound is determined by many things, but most significantly it is impacted by the stability of the conjugate base, that is mainly determined by the ability (or inability) of the conjugated base to stabilize the negative charge. The negative charge is stabilized when it is distributed on a large surface or a long chain. One of the mechanisms that distributes the negative charge on a longer chain or a ring is resonance. Solvent also could assist in the stabilization of the negative charge on a conjugated base.

Bases used to deprotonate depend on the pK_a of the compound. Where the proton is not particularly acidic

Acid

An acid is traditionally considered any chemical compound that, when dissolved in water, gives a solution with a hydrogen ion Activity greater than in pure water, i.e....
, and as such, the molecule does not give up its proton easily, a base stronger than the commonly known hydroxide

Hydroxide

In chemistry, hydroxide is the name for the Diatomic molecule anion OH-, consisting of oxygen and hydrogen atoms, usually derived from the Dissociation of a base ....
s are required. Hydride

Hydride

Hydride is the name given to the Electric charge ion of hydrogen, H-. Although this ion does not exist except in extraordinary conditions, the term hydride is widely applied to describe Chemical compound of hydrogen with other chemical element, particularly those of Periodic table group 1–16....
s are one of the many types of powerful deprotonating agents. Common hydrides used are sodium hydride

Sodium hydride

Sodium hydride is the chemical compound with the formula NaH. It is primarily used as a strong base in organic synthesis. NaH is representative of the saline hydrides, meaning it is a salt-like hydride, composed of Na+ and H- ions, in contrast to the more molecular hydrides such as borane, methane, ammonia and water....
and potassium hydride

Potassium hydride

Potassium hydride, KH, is a chemical compound of potassium and hydrogen. It is a hydride of potassium. It reacts with water according to the reaction:...
. These bases are so powerful because the hydride forms hydrogen

Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
gas

Gas

In physics, a gas is a state of matter, consisting of a collection of particles without a definite shape or volume that are in more or less random motion....
when the proton from the other molecule is removed. However, the production of hydrogen also means that deprotonation using agents that release hydrogen are dangerous and should be done in an inert

Inert

In English, to be inert is to be in a state of doing little or nothing....
atmosphere

Atmosphere

An atmosphere is a layer of gases that may surround a material body of sufficient mass, by the gravity of the body, and are retained for a longer duration if gravity is high and the atmosphere's temperature is low....
(e.g. nitrogen

Nitrogen

Nitrogen is a chemical element that has the symbol N and atomic number 7 and atomic mass 14.00674?. Elemental nitrogen is a colorless, odorless, tasteless and mostly inert diatomic gas at standard conditions, constituting 78% by volume of Earth's atmosphere....
) as water is a source of protons that is present in the air around us all the time and may react with the hydride instead of the desired molecule or may set on fire.

Deprotonation

See also