Methyldiazonium: Difference between revisions
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'''Methyldiazonium''' is an [[organic compound]] consisting of a [[methyl group]] attached to a [[diazo group]]. This [[cation]]ic chemical is the [[conjugate acid]] of [[diazomethane]], wih an estimated [[pKa|p''K''<sub>a</sub>]]<10.<ref>{{Cite journal|last1=Fei|first1=Na|last2=Sauter|first2=Basilius|last3=Gillingham|first3=Dennis|date=2016|title=The p''K''<sub>a</sub> of Brønsted acids controls their reactivity with diazo compounds|journal=Chemical Communications|language=en|volume=52|issue=47|pages=7501–7504|doi=10.1039/C6CC03561B|pmid=27212133|doi-access=free}}</ref> It is an [[chemical intermediate|intermediate]] in methylation reactions of diazomethane with acidic hydroxyl compounds, such as conversion of [[carboxylic acid]]s to [[methyl ester]]s and [[phenol]]s to [[methyl ether]]s.<ref>{{cite journal |title= Mechanism of Methyl Esterification of Carboxylic Acids by Trimethylsilyldiazomethane |first1= Erik |last1= Kühnel |first2= David D. P. |last2= Laffan |first3= Guy C. |last3= Lloyd-Jones |first4= Teresa |last4= Martínez del Campo |first5= Ian R. |last5= Shepperson |first6= Jennifer L. |last6= Slaughter |doi= 10.1002/anie.200702131 |journal= Angew. Chem. Int. Ed. Engl. |volume= 46 |issue= 37 |year= 2007 |pages= 7075–7078 |pmid= 17691089 }}</ref> It has been implicated as the [[metabolism|metabolite]] of [[N-Nitrosodimethylamine|''N''-nitrosodimethylamine]] responsible for the observed [[carcinogenicity]] of that compound.<ref name=Tricker>{{cite journal |pmid=2017213 |title= Carcinogenic ''N''-nitrosamines in the Diet: Occurrence, Formation, Mechanisms and Carcinogenic Potential |journal= Mutation Research/Genetic Toxicology |volume= 259 |issue= 3–4 |pages= 277–289 |year= 1991 |last1= Tricker |first1= A. R. |last2= Preussmann |first2= R. |doi= 10.1016/0165-1218(91)90123-4 }}</ref> |
'''Methyldiazonium''' is an [[organic compound]] consisting of a [[methyl group]] attached to a [[diazo group]]. This [[cation]]ic chemical is the [[conjugate acid]] of [[diazomethane]], wih an estimated [[pKa|p''K''<sub>a</sub>]]<10.<ref>{{Cite journal|last1=Fei|first1=Na|last2=Sauter|first2=Basilius|last3=Gillingham|first3=Dennis|date=2016|title=The p''K''<sub>a</sub> of Brønsted acids controls their reactivity with diazo compounds|journal=Chemical Communications|language=en|volume=52|issue=47|pages=7501–7504|doi=10.1039/C6CC03561B|pmid=27212133|doi-access=free}}</ref> |
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:[[File:Methyldiazonium acidity equilibrium.png|300px]] |
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It is an [[chemical intermediate|intermediate]] in methylation reactions of diazomethane with acidic hydroxyl compounds, such as conversion of [[carboxylic acid]]s to [[methyl ester]]s and [[phenol]]s to [[methyl ether]]s.<ref>{{cite journal |title= Mechanism of Methyl Esterification of Carboxylic Acids by Trimethylsilyldiazomethane |first1= Erik |last1= Kühnel |first2= David D. P. |last2= Laffan |first3= Guy C. |last3= Lloyd-Jones |first4= Teresa |last4= Martínez del Campo |first5= Ian R. |last5= Shepperson |first6= Jennifer L. |last6= Slaughter |doi= 10.1002/anie.200702131 |journal= Angew. Chem. Int. Ed. Engl. |volume= 46 |issue= 37 |year= 2007 |pages= 7075–7078 |pmid= 17691089 }}</ref> It has been implicated as the [[metabolism|metabolite]] of [[N-Nitrosodimethylamine|''N''-nitrosodimethylamine]] responsible for the observed [[carcinogenicity]] of that compound.<ref name=Tricker>{{cite journal |pmid=2017213 |title= Carcinogenic ''N''-nitrosamines in the Diet: Occurrence, Formation, Mechanisms and Carcinogenic Potential |journal= Mutation Research/Genetic Toxicology |volume= 259 |issue= 3–4 |pages= 277–289 |year= 1991 |last1= Tricker |first1= A. R. |last2= Preussmann |first2= R. |doi= 10.1016/0165-1218(91)90123-4 }}</ref> |
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== References == |
== References == |
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Revision as of 03:35, 22 June 2024
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| CH3N2+ | |
| Molar mass | 43.048 g·mol−1 |
| Related compounds | |
Related compounds
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Diazomethane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
- ^ 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.
- ^ 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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