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It is the conjugate acid of pyridine. Many related cations are known involving substituted pyridines, e.g. picolines, lutidines, collidines. They are prepared by treating pyridine with acids. [3] As pyridine is often used as an organic base in chemical reactions, pyridinium salts are produced in many acid-base reactions.
Pyridine is a Lewis base, donating its pair of electrons to a Lewis acid. Its Lewis base properties are discussed in the ECW model . Its relative donor strength toward a series of acids, versus other Lewis bases, can be illustrated by C-B plots .
In organic synthesis, PPTS is used as a weakly acidic catalyst, providing an organic soluble source of pyridinium (C 5 H 5 NH +) ions.For example, PPTS is used to deprotect silyl ethers or tetrahydropyranyl ethers when a substrate is unstable to stronger acid catalysts.
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]
With a pK a of 5.25 for its conjugate acid, pyridine is about 15x less basic than imidazole. Pyridine is a weak pi-acceptor ligand. Trends in the M-N distances for complexes of the type [MCl 2 (py) 4] 2+ reveal an anticorrelation with d-electron count. [2] Few low-valent metal complexes of pyridines are known.
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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.
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