An overview of the
Pyridine (formula C6H5N) containing a nitrogen heteroatom six-member heterocyclic compounds, one of the benzene molecule - CH = be replaced by nitrogen compounds generated, like benzene, have the same electronic structure, still have aromaticity, so it is also called nitrogen impurity benzene, benzene and nitrogen at room temperature is a colorless liquid, with special smell - 41.6 ℃, melting point, boiling point 115.2 ℃, and water form azeotrope, boiling point of 92 ~ 93 ℃. (Industrial use of this property to purify pyridine), the density of 0.9819g/cm3. Soluble in water, ethanol, ether and other organic solvents, itself can also be used as a solvent.
Pyridine was originally isolated from bone tar. Later, coal tar, gas, shale oil and petroleum also contain pyridine and its homologues, such as 2-methylpyridine and 2, 6-dimethylpyridine.
Pyridine and its derivatives are more stable than benzene and have similar reactivity to nitrobenzene. Due to the electron absorption of nitrogen atoms in the ring, the electron density at positions 2, 4 and 6 is lower than that at positions 3 and 5. The typical electrophilic substitution reaction of aromatic groups occurs at positions 3 and 5, but the reactivity is lower than that of benzene, and nitrification, halogenation, sulfonation and other reactions are generally not easy to occur.
In addition, these substitution reactions take place in an acidic medium, where pyridine forms positively charged ions, making the electrophile inaccessible. The halogens of 2- or 4- halopyridine are both active. Due to the low electron density at positions 2 and 6, nucleophilic substitution reactions can occur at this position, such as with sodium amine or potassium hydroxide, to obtain the corresponding 2-aminopyridine or 2-hydroxy pyridine. Pyridine is also used industrially as a denaturing agent, as a dye aid, and as a starting point for the synthesis of a range of products, including pharmaceuticals, disinfectants, dyes, food flavorings, adhesives, explosives, and so on. Pyridine is toxic and can reduce male fertility by inhalation, ingestion or skin contact. It can also cause cancer. Pyridine is a weak tertiary amine, in ethanol solution with a variety of acids (such as picric or perchloric acid, etc.) to form an insoluble salt. Industrial pyridines contain about 1% of 2-methylpyridine, so differences in salting properties can be used to separate them from their homologues. Pyridine can also form crystalline complexes with a variety of metal ions.
Pyridine is more easily reduced than benzene, such as to hexahydropyridine (or piperidine) in the presence of sodium metal and ethanol.
Pyridine with hydrogen peroxide reaction, easy to be oxidized to pyridine N - oxidation, N - oxide pyridine is an important pyridine derivatives, due to the nitrogen atoms are after oxidation, cannot form a positively charged pyridine ions, thus is advantageous to the aromatic electrophilic substitution reaction, instead of after, again to remove nitrogen in oxygen, can be directly replaced by pyridine derivatives can't get by.