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imidazole : ウィキペディア英語版
imidazole

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Imidazole is an organic compound with the formula (CH)2N(NH)CH. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole.
Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles, share the 1,3-C3N2 ring but feature varied substituents. This ring system is present in important biological building-blocks, such as histidine, and the related hormone histamine. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.〔Alan R. Katritzky; Rees. ''Comprehensive Heterocyclic Chemistry.'' Vol. 5, p.469-498, (1984).〕〔Grimmett, M. Ross. ''Imidazole and Benzimidazole Synthesis.'' Academic Press, (1997).〕〔Brown, E.G. ''Ring Nitrogen and Key Biomolecules.'' Kluwer Academic Press, (1998).〕〔Pozharskii, A.F, et al. ''Heterocycles in Life and Society.'' John Wiley & Sons, (1997).〕〔Heterocyclic Chemistry TL Gilchrist, The Bath press 1985 ISBN 0-582-01421-2〕
When fused to a pyrimidine ring, it forms purine, which is the most widely occurring nitrogen-containing heterocycle in nature.
==Structure and properties==
Imidazole is a planar 5-membered ring. It exists in two equivalent tautomeric forms, because the positive charge can be located on either of the two nitrogen atoms. Imidazole is a highly polar compound, as evidenced by a calculated dipole of 3.61D. It is highly soluble in water. The compound is classified as aromatic due to the presence of a sextet of π-electrons, consisting of a pair of electrons from the protonated nitrogen atom and one from each of the remaining four atoms of the ring. Some resonance structures of imidazole are shown below:


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