Imidazole

File:Imidazole-3D-balls.png

Ball-and-stick model of imidazole. White balls are hydrogen atoms, black balls are carbon atoms, and blue balls are nitrogen atoms. The

Imidazole (ImH) is an organic compound. It is an aromatic ring with five atoms, three carbon and two nitrogen. Its chemical formula is C
3H
4N
2 or C
3H
3(NH)N. Imidazole is an aromatic compound. It is a white or colourless solid at 25 degrees Celsius at standard atmosphere (a pressure). It i is soluble in water, producing a mildly alkaline solution.

Role in biology

Many natural products, especially alkaloids, have the imidazole ring. This ring system is present in important biological building blocks, such as histidine, and the related hormone, histamine.

Properties

Only one of the nitrogen atoms in imidizole acts as a base. The other nitrogen atom is bonded to a hydrogen atom that acts like a weak acid. Because it can be both an acid and a base, imidazole is amphoteric.

Imidazole Media

• Resonance-imidazole.svg

  Resonance structures of imidazole.

• Imidazole from glyoxal aldehyde ammonia.svg

  Imidazole from glyoxal aldehyde ammonia

• Imidazole one-bond-method.svg

  Imidazole one-bond-method: Synthesis of imidazole from an imidate and an α-aminoaldehyde or α-aminoacetal.

• Imidazole two-bond-method.svg

  Formation of imidazole derivates from a 1,2-diaminoalkane and a carboxylic acid using Pt as a dehydrogenating catalyst.

• (1,2)(3,4) formation imidazole.svg

  Formation of the (1,2) and (3,4) bonds of imidazole derivatives from N-substituted α-aminoketones and formamide.

• Debus-Radziszewski imidazole synthesis.svg

  Debus-Radziszewski imidazole synthesis. Formation of imidazole from glyoxal, aldehyde, amine, and ammonia.

• Imidazole synthesis from vinyltetrazole.svg

  Imidazole synthesis from vinyltetrazole

• Prochloraz.svg

  Prochloraz is one of several imidazole-derived agrichemicals.

• Imidazolium salt.svg

  Imidazolium salt