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Pyrrole is an extremely weak base for an amine, with a conjugate acid pK a of −3.8. The most thermodynamically stable pyrrolium cation (C 4 H 6 N +) is formed by protonation at the 2 position. Substitution of pyrrole with alkyl substituents provides a more basic molecule—for example, tetramethylpyrrole has a conjugate acid pK a of +3.7.
For example, acetic acid is a weak acid which has a = 1.75 x 10 −5. Its conjugate base is the acetate ion with K b = 10 −14 /K a = 5.7 x 10 −10 (from the relationship K a × K b = 10 −14), which certainly does not correspond to a strong base. The conjugate of a weak acid is often a weak base and vice versa.
On the other hand, if a chemical is a weak acid its conjugate base will not necessarily be strong. Consider that ethanoate, the conjugate base of ethanoic acid, has a base splitting constant (Kb) of about 5.6 × 10 −10, making it a weak base. In order for a species to have a strong conjugate base it has to be a very weak acid, like water.
with regards to acid-base reactions, electron-rich species have high pKa's and react with weak Lewis acids. [4] with regards to nucleophilic substitution reactions, electron-rich species are relatively strong nucleophiles, as judged by rates of attack by electrophiles. For example, compared to benzene, pyrrole is more rapidly attacked by ...
A strong base is a basic chemical compound that can remove a proton (H +) from (or deprotonate) a molecule of even a very weak acid (such as water) in an acid–base reaction. Common examples of strong bases include hydroxides of alkali metals and alkaline earth metals, like NaOH and Ca(OH) 2, respectively. Due to their low solubility, some ...
The position of equilibrium varies from base to base when a weak base reacts with water. The further to the left it is, the weaker the base. [5] When there is a hydrogen ion gradient between two sides of the biological membrane, the concentration of some weak bases are focused on only one side of the membrane. [6]
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Similarly the strength of a strong base is leveled by the acidity of the solvent. When a strong acid is dissolved in water, it reacts with it to form hydronium ion (H 3 O +). [2] An example of this would be the following reaction, where "HA" is the strong acid: HA + H 2 O → A − + H 3 O + Any acid that is stronger than H 3 O + reacts with H ...