Imidazole
Imidazole is an organic compound with the formula C3H4N2. This aromatic heterocyclic is a diazole and one of the fundamental units of the vast class of histidine and histamine.
Structure and properties[edit | edit source]
Imidazole is a 5-membered planar ring, which is soluble in water and forms a tautomeric equilibrium. That is, the compound can be represented by two tautomeric chemical structures, the aromatic one being more stable than the open-chain form.
Preparation[edit | edit source]
Imidazole can be synthesized by numerous methods besides the Debus method. Many of these syntheses can also be applied to different substituted imidazoles.
Applications[edit | edit source]
Imidazole is incorporated into many important biological molecules. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.
Safety[edit | edit source]
Imidazole is amphoteric, that is, it can function as both an acid and as a base. As an acid, the pKa of imidazole is 14.05, making it less acidic than carboxylic acids, phenols, and imides, but slightly more acidic than alcohols.
See also[edit | edit source]
References[edit | edit source]
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Contributors: Prab R. Tumpati, MD