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diazo : ウィキペディア英語版
diazo

Diazo refers to a type of organic compound called diazo compound that has two linked nitrogen atoms (azo) as a terminal functional group. The general formula is R2C=N2. The simplest example of a diazo compound is diazomethane. The electronic structure of diazo compounds involves a positive charge on the central nitrogen and negative charge distributed between the terminal nitrogen and the carbon. Some of the most stable diazo compounds are α-diazo-ß-diketones and α-diazo-ß-diesters since the negative charge is delocalized into the carbonyls. In contrast, most alkyldiazo compounds are explosive. A commercially relevant diazo compound is ethyl diazoacetate (N2CHCOOEt). A group of isomeric compounds with only few similar properties are the diazirines, where the carbon and two nitrogens are linked as a ring.
Four resonance structures can be drawn:〔F.A. Carey R.J. Sundberg ''Advanced Organic Chemistry'', 2nd Edition〕
:
Diazo compounds should not be confused with azo compounds of the type R-N=N-R or with diazonium compounds of the type R-N2+.
==History==
Diazo compounds were first produced by Peter Griess who had discovered a versatile new chemical reaction, as detailed in his "preliminary notice on the influence of nitrous acid on aminonitro- and aminodinitrophenol."
〔Trevor I. Williams, ‘Griess, (Johann) Peter (1829–1888)’, Oxford Dictionary of National Biography, Oxford University Press, 2004〕

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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