Jump to content

Methyldiazonium

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by DMacks (talk | contribs) at 22:03, 21 June 2024 ("Cation" and "carbon-containing", but the C is definitely not the +). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Methyldiazonium is an organic compound consisting of a methyl group attached to a diazo group. This cationic chemical is the conjugate acid of diazomethane, wih an estimated pKa<10.[1] 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] It has been implicated as the metabolite of N-nitrosodimethylamine responsible for the observed carcinogenicity of that compound.[3]

References

  1. ^ Fei, Na; Sauter, Basilius; Gillingham, Dennis (2016). "The pKa of Brønsted acids controls their reactivity with diazo compounds". Chemical Communications. 52 (47): 7501–7504. doi:10.1039/C6CC03561B. PMID 27212133.
  2. ^ 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.
  3. ^ 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.


Stub icon

This organic chemistry article is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/enwiki/w/index.php?title=Methyldiazonium&oldid=1230297255"