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Pyridinium

 

 
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Pyridinium
 
 
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Pyridinium refers to the cationic form of pyridine
Pyridine

Pyridine is a simple and important heterocyclic aromatic organic compound with the formula CarbonHydrogenNitrogen. This colorless liquid with a distinctive fish-like odor is structurally related to benzene, wherein one CH group in the six-membered ring is replaced by a nitrogen atom....
. This can either be due to protonation
Protonation

In chemistry, protonation is the addition of a proton to an atom, molecule, or ion. Protonation is possibly the most fundamental chemical reaction and is a step in many stoichiometry and catalysis....
 of the ring nitrogen or because of addition of a substituent to the ring nitrogen, typically via alkylation
Alkylation

Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene ....
. The lone pair
Lone pair

A lone pair is a valence electron pair without bonding or sharing with other atoms. They are found in the outermost electron shell of an atom, so lone pairs are a subset of a molecule's valence electrons....
 of electron
Electron

The electron is a subatomic particle that carries a negative electric charge. It has elementary particle and is believed to be a point particle....
s on the 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....
 atom
Atom

|-! bgcolor=gray | Properties|-||}The atom is a basic unit of matter consisting of a dense, central atomic nucleus surrounded by a electron cloud of electric charge electrons....
 of pyridine is not delocalized, and thus pyridine can be protonated easily. Pyridine is often used as an organic base in chemical reations, thus the pyridinium ion
Ion

An ion is an atom or molecule which has lost or gained one or more electrons, giving it a positive or negative electrical charge. According to the Bohr_model this will be from or in the outer shield 'n'....
 is produced as the counter ion to the leaving group in the reaction.






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Pyridinium refers to the cationic form of pyridine
Pyridine

Pyridine is a simple and important heterocyclic aromatic organic compound with the formula CarbonHydrogenNitrogen. This colorless liquid with a distinctive fish-like odor is structurally related to benzene, wherein one CH group in the six-membered ring is replaced by a nitrogen atom....
. This can either be due to protonation
Protonation

In chemistry, protonation is the addition of a proton to an atom, molecule, or ion. Protonation is possibly the most fundamental chemical reaction and is a step in many stoichiometry and catalysis....
 of the ring nitrogen or because of addition of a substituent to the ring nitrogen, typically via alkylation
Alkylation

Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene ....
. The lone pair
Lone pair

A lone pair is a valence electron pair without bonding or sharing with other atoms. They are found in the outermost electron shell of an atom, so lone pairs are a subset of a molecule's valence electrons....
 of electron
Electron

The electron is a subatomic particle that carries a negative electric charge. It has elementary particle and is believed to be a point particle....
s on the 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....
 atom
Atom

|-! bgcolor=gray | Properties|-||}The atom is a basic unit of matter consisting of a dense, central atomic nucleus surrounded by a electron cloud of electric charge electrons....
 of pyridine is not delocalized, and thus pyridine can be protonated easily. Pyridine is often used as an organic base in chemical reations, thus the pyridinium ion
Ion

An ion is an atom or molecule which has lost or gained one or more electrons, giving it a positive or negative electrical charge. According to the Bohr_model this will be from or in the outer shield 'n'....
 is produced as the counter ion to the leaving group in the reaction. This complex is often insoluble in the organic solvent, so precipitation of the pyridinium leaving group complex is an indication of the progress of the reaction. The pyridinium ion also plays a role in Friedel-Crafts acylation. When pyridine is included, it forms a complex with the electrophillic acylium ion, rendering it even more reactive.

See also

  • Pyridinium chlorochromate
    Pyridinium chlorochromate

    Pyridinium chlorochromate is a reddish orange solid reagent used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones. Pyridinium chlorochromate, or PCC, will not fully oxidize the alcohol to the carboxylic acid as does the Jones reagent....