Methyldiazonium
Topic: Chemistry
From HandWiki - Reading time: 1 min
Methyldiazonium is an organic compound consisting of a methyl group attached to a diazo group. This cation is the conjugate acid of diazomethane, with an estimated pKa<10.[1]
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It is an intermediate in methylation reactions of diazomethane with acidic hydroxyl compounds, such as conversion of carboxylic acids to methyl esters and phenols to methyl ethers.[2]
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It has been implicated as the metabolite of N-nitrosodimethylamine responsible for the observed carcinogenicity of that compound.[3]
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References
- ↑ Fei, Na; Sauter, Basilius; Gillingham, Dennis (2016). "The pKa of Brønsted acids controls their reactivity with diazo compounds" (in en). Chemical Communications 52 (47): 7501–7504. doi:10.1039/C6CC03561B. PMID 27212133.
- ↑ Kühnel, Erik; Laffan, David D. P.; Lloyd-Jones, Guy C.; Martínez del Campo, Teresa; Shepperson, Ian R.; Slaughter, Jennifer L. (2007). "Mechanism of Methyl Esterification of Carboxylic Acids by Trimethylsilyldiazomethane". Angew. Chem. Int. Ed. Engl. 46 (37): 7075–7078. doi:10.1002/anie.200702131. PMID 17691089.
- ↑ Tricker, A. R.; Preussmann, R. (1991). "Carcinogenic N-nitrosamines in the Diet: Occurrence, Formation, Mechanisms and Carcinogenic Potential". Mutation Research/Genetic Toxicology 259 (3–4): 277–289. doi:10.1016/0165-1218(91)90123-4. PMID 2017213.
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