Definitions for deprotonation
de·pro·to·na·tion

WiktionaryRate this definition:0.0 / 0 votes

1. deprotonationnoun

   The removal of a proton (hydrogen ion) from a molecule to form a conjugate base

WikipediaRate this definition:0.0 / 0 votes

1. Deprotonation

   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. The species formed is the conjugate base of that acid. The complementary process, when a proton is added (transferred) to a Brønsted–Lowry base, is protonation (or hydronation). The species formed is the conjugate acid of that base. A species that can either accept or donate a proton is referred to as amphiprotic. An example is the H2O (water) molecule, which can gain a proton to form the hydronium ion, H3O+, or lose a proton, leaving the hydroxide ion, OH−. The relative ability of a molecule to give up a proton is measured by its pKa value. A low pKa value indicates that the compound is acidic and will easily give up its proton to a base. The pKa of a compound is determined by many aspects, but the most significant is the stability of the conjugate base. This is primarily determined by the ability (or inability) of the conjugated base to stabilize negative charge. One of the most important ways of assessing a conjugate base's ability to distribute negative charge is using resonance. Electron withdrawing groups (which can stabilize the molecule by increasing charge distribution) or electron donating groups (which destabilize by decreasing charge distribution) present on a molecule also determine its pKa. The solvent used can also assist in the stabilization of the negative charge on a conjugated base. Bases used to deprotonate depend on the pKa of the compound. When the compound is not particularly acidic, and, as such, the molecule does not give up its proton easily, a base stronger than the commonly known hydroxides is required. Hydrides are one of the many types of powerful deprotonating agents. Common hydrides used are sodium hydride and potassium hydride. The hydride forms hydrogen gas with the liberated proton from the other molecule. The hydrogen is dangerous and could ignite with the oxygen in the air, so the chemical procedure should be done in an inert atmosphere (e.g., nitrogen). Deprotonation can be an important step in a chemical reaction. Acid–base reactions typically occur faster than any other step which may determine the product of a reaction. The conjugate base is more electron-rich than the molecule which can alter the reactivity of the molecule. For example, deprotonation of an alcohol forms the negatively charged alkoxide, which is a much stronger nucleophile. To determine whether or not a given base will be sufficient to deprotonate a specific acid, compare the conjugate base with the original base. A conjugate base is formed when the acid is deprotonated by the base. In the image above, hydroxide acts as a base to deprotonate the carboxylic acid. The conjugate base is the carboxylate salt. In this case, hydroxide is a strong enough base to deprotonate the carboxylic acid because the conjugate base is more stable than the base because the negative charge is delocalized over two electronegative atoms compared to one. Using pKa values, the carboxylic acid is approximately 4 and the conjugate acid, water, is 15.7. Because acids with higher pKa values are less likely to donate their protons, the equilibrium will favor their formation. Therefore, the side of the equation with water will be formed preferentially. If, for example, water, instead of hydroxide, was used to deprotonate the carboxylic acid, the equilibrium would not favor the formation of the carboxylate salt. This is because the conjugate acid, hydronium, has a pKa of -1.74, which is lower than the carboxylic acid. In this case, equilibrium would favor the carboxylic acid.

WikidataRate this definition:0.0 / 0 votes

1. Deprotonation

   Deprotonation is the removal of a proton from a molecule, forming the conjugate base. The relative ability of a molecule to give up a proton is measured by its pKa value. A low pKa value indicates that the compound is acidic and will easily give up its proton to a base. The pKa of a compound is determined by many things, but the most significant is the stability of the conjugate base, which is determined mainly by the ability 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 distribute the negative charge on a longer chain or a ring is resonance. The solvent can also assist in the stabilization of the negative charge on a conjugated base. Bases used to deprotonate depend on the pKa of the compound. When the compound is not particularly acidic, and, as such, the molecule does not give up its proton easily, a base stronger than the commonly known hydroxides is required. Hydrides are one of the many types of powerful deprotonating agents. Common hydrides used are sodium hydride and potassium hydride. The hydride forms hydrogen gas with the proton from the other molecule. However, the production of hydrogen also means that deprotonation using agents that release hydrogen is dangerous and should be done in an inert atmosphere, as the hydrogen can ignite with the oxygen in the air.

How to pronounce deprotonation?

1. Alex

   US English

   David

   US English

   Mark

   US English

   Daniel

   British

   Libby

   British

   Mia

   British

   Karen

   Australian

   Hayley

   Australian

   Natasha

   Australian

   Veena

   Indian

   Priya

   Indian

   Neerja

   Indian

   Zira

   US English

   Oliver

   British

   Wendy

   British

   Fred

   US English

   Tessa

   South African

How to say deprotonation in sign language?

Numerology

1. Chaldean Numerology

   The numerical value of deprotonation in Chaldean Numerology is: 6

2. Pythagorean Numerology

   The numerical value of deprotonation in Pythagorean Numerology is: 4

Popularity rank by frequency of use

References

1. ^ Wiktionary
   https://en.wiktionary.org/wiki/Deprotonation
2. ^ Wikipedia
   https://en.wikipedia.org/wiki/Deprotonation
3. ^ Wikidata
   https://www.wikidata.org/w/index.php?search=deprotonation