Pyridine: Difference between revisions
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{{Short description|A basic heterocyclic organic compound}} | |||
{{Chembox | |||
| Name = Pyridine | |||
| ImageFile = Pyridine-2D-skeletal.png | |||
| ImageSize = 150px | |||
| ImageAlt = Skeletal formula of pyridine | |||
| ImageFile1 = Pyridine-3D-balls.png | |||
| ImageSize1 = 150px | |||
| ImageAlt1 = Ball-and-stick model of pyridine | |||
| IUPACName = Pyridine | |||
| OtherNames = Azabenzene, Azine | |||
| Section1 = {{Chembox Identifiers | |||
| CASNo = 110-86-1 | |||
| PubChem = 1049 | |||
| ChemSpiderID = 1023 | |||
| UNII = 8J337D1HZY | |||
| KEGG = C11382 | |||
| ChEBI = 16227 | |||
| ChEMBL = 15830 | |||
| SMILES = C1=CC=NC=C1 | |||
| InChI = 1S/C5H5N/c1-2-4-6-5-3-1/h1-5H | |||
| InChIKey = JUJWROOIHBZHMG-UHFFFAOYSA-N | |||
}} | |||
| Section2 = {{Chembox Properties | |||
| C=5 | |||
| H=5 | |||
| N=1 | |||
| Appearance = Colorless liquid | |||
| Density = 0.9819 g/cm_ | |||
| MeltingPt = _41.6 °C | |||
| BoilingPt = 115.2 °C | |||
| Solubility = Miscible with water | |||
}} | |||
}} | |||
==Overview== | |||
[[Pyridine]] is a basic heterocyclic organic compound with the chemical formula C_H_N. It is structurally related to [[benzene]], with one methine group (=CH_) replaced by a nitrogen atom. Pyridine is a colorless liquid with a distinct, unpleasant fish-like odor. It is miscible with water and most organic solvents. | |||
Pyridine is | ==Structure and Properties== | ||
Pyridine is a six-membered ring containing five carbon atoms and one nitrogen atom. The presence of the nitrogen atom in the ring makes pyridine a weak base, with a pKa of 5.25 for its conjugate acid. The nitrogen atom contributes a lone pair of electrons, which can participate in hydrogen bonding and coordination to metal ions. | |||
[[File:Pyridine-3D-balls.png|thumb|left|Ball-and-stick model of pyridine]] | |||
Pyridine | |||
The aromaticity of pyridine is similar to that of benzene, with the nitrogen atom contributing to the delocalized π-electron system. This aromaticity is responsible for the stability of the pyridine ring. | |||
== | ==Synthesis== | ||
Pyridine | Pyridine can be synthesized through several methods, including the [[Chichibabin synthesis]], which involves the reaction of aldehydes, ammonia, and formaldehyde. Another method is the [[Bönnemann cyclization]], which uses acetylene and hydrogen cyanide. | ||
== | ==Applications== | ||
Pyridine is | Pyridine is used as a precursor to agrochemicals and pharmaceuticals. It is also a solvent and reagent in organic synthesis. Pyridine derivatives are found in many drugs, including [[antihistamines]], [[antibiotics]], and [[antidepressants]]. | ||
== | ==Safety== | ||
* [[ | Pyridine is toxic and can be harmful if inhaled, ingested, or absorbed through the skin. It can cause irritation to the eyes, skin, and respiratory tract. Proper safety precautions should be taken when handling pyridine. | ||
* [[ | |||
* [[ | ==Related pages== | ||
* [[ | * [[Benzene]] | ||
* [[Heterocyclic compound]] | |||
* [[Aromaticity]] | |||
* [[Chichibabin synthesis]] | |||
[[Category:Heterocyclic compounds]] | [[Category:Heterocyclic compounds]] | ||
[[Category: | [[Category:Solvents]] | ||
[[Category:Organic chemistry]] | |||
Latest revision as of 17:43, 18 February 2025
A basic heterocyclic organic compound
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Overview[edit]
Pyridine is a basic heterocyclic organic compound with the chemical formula C_H_N. It is structurally related to benzene, with one methine group (=CH_) replaced by a nitrogen atom. Pyridine is a colorless liquid with a distinct, unpleasant fish-like odor. It is miscible with water and most organic solvents.
Structure and Properties[edit]
Pyridine is a six-membered ring containing five carbon atoms and one nitrogen atom. The presence of the nitrogen atom in the ring makes pyridine a weak base, with a pKa of 5.25 for its conjugate acid. The nitrogen atom contributes a lone pair of electrons, which can participate in hydrogen bonding and coordination to metal ions.
The aromaticity of pyridine is similar to that of benzene, with the nitrogen atom contributing to the delocalized π-electron system. This aromaticity is responsible for the stability of the pyridine ring.
Synthesis[edit]
Pyridine can be synthesized through several methods, including the Chichibabin synthesis, which involves the reaction of aldehydes, ammonia, and formaldehyde. Another method is the Bönnemann cyclization, which uses acetylene and hydrogen cyanide.
Applications[edit]
Pyridine is used as a precursor to agrochemicals and pharmaceuticals. It is also a solvent and reagent in organic synthesis. Pyridine derivatives are found in many drugs, including antihistamines, antibiotics, and antidepressants.
Safety[edit]
Pyridine is toxic and can be harmful if inhaled, ingested, or absorbed through the skin. It can cause irritation to the eyes, skin, and respiratory tract. Proper safety precautions should be taken when handling pyridine.
