AskDefine | Define nitrofuran

Dictionary Definition

nitrofuran n : derivative of furan used to inhibit bacterial growth

User Contributed Dictionary

English

Noun

  1. A class of drug, deried from furan, used to inhibit bacterial growth.

Derived terms

Extensive Definition

Furan, also known as furane and furfuran, is a heterocyclic organic compound. It is typically derived by the thermal decomposition of pentose-containing materials, cellulosic solids especially pine-wood. Furan is a colorless, flammable, highly volatile liquid with a boiling point close to room temperature. It is toxic and may be carcinogenic. Catalytic hydrogenation (see redox) of furan with a palladium catalyst gives tetrahydrofuran.

History

The name furan comes from the Latin furfur, which means bran. The first furan derivative to be described was 2-furoic acid, by Carl Wilhelm Scheele in 1780. Another important derivative, furfural, was reported by Johann Wolfgang Döbereiner in 1831 and characterised nine years later by John Stenhouse. Furan itself was first prepared by Heinrich Limpricht in 1870, although he called it tetraphenol. REFRENCES.

Synthesis and isolation

Chemistry

Furan is aromatic because one of the lone pairs of electrons on the oxygen atom is delocalized into the ring, creating a 4n+2 aromatic system (see Hückel's rule) similar to benzene. Because of the aromaticity, the molecule is flat and lacks discrete double bonds. The other lone pair of electrons of the oxygen atom extends in the plane of the flat ring system. The sp2 hybridization is to allow one of the lone pairs of oxygen to reside in a p orbital and thus allow it to interact within the pi-system.
Due to its aromaticity, furan's behavior is quite dissimilar to that of the more typical heterocyclic ethers such as tetrahydrofuran.
  • It is considerably more reactive than benzene in electrophilic substitution reactions, due to the electron-donating effects of the oxygen heteroatom. Examination of the resonance contributors shows the increased electron density of the ring, leading to increased rates of electrophilic substitution.
  • Furan serves as a diene in Diels-Alder reactions with electron-deficient dienophiles such as ethyl (E)-3-nitroacrylate. The reaction product is a mixture of isomers with preference for the endo isomer:

See also

nitrofuran in German: Furan
nitrofuran in Spanish: Furano
nitrofuran in French: Furane
nitrofuran in Italian: Furano
nitrofuran in Latvian: Furāns
nitrofuran in Dutch: Furaan
nitrofuran in Japanese: フラン (化学)
nitrofuran in Norwegian: Furan
nitrofuran in Polish: Furan
nitrofuran in Portuguese: Furano (química)
nitrofuran in Russian: Фуран
nitrofuran in Slovak: Furán
nitrofuran in Finnish: Furaani
nitrofuran in Swedish: Furan
nitrofuran in Vietnamese: Furan
nitrofuran in Turkish: Furan
nitrofuran in Ukrainian: Фуран
nitrofuran in Chinese: 呋喃
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