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{{Chembox
{{Chembox
<!-- Images -->
<!-- Images -->| ImageFile = Methyldiazonium.png
| ImageCaption =
| ImageFile = Methyldiazonium.png
| ImageCaption =
| OtherNames =
| IUPACName = Methyldiazynium
|Section1={{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| CASNo = 20404-06-2
| CASNo = 20404-06-2
| ChEBI = 176914
| ChEBI = 176914
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| SMILES = C[N+]#N
| SMILES = C[N+]#N
}}
}}
|Section2={{Chembox Properties
| Section2 = {{Chembox Properties
|C=1|H=3|N=2|Formula_Charge=+
|C=1|H=3|N=2|Formula_Charge=+
|pKa = <10
}}
|ConjugateBase = [[Diazomethane]]
|Section8={{Chembox Related
| OtherCompounds = [[Diazomethane]]
}}
}}
}}
}}


'''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>
'''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|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>
:[[File:Methyldiazonium acidity equilibrium.png|300px]]
:[[File:Methyldiazonium acidity equilibrium.png|250px]]
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>
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>
:[[File:Diazomethanemethylation.png|400px]]
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>
:[[File:Ndma activ.svg|400px]]


== References ==
== References ==
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[[Category:Cations]]
[[Category:Cations]]
[[Category:Methylating agents]]
[[Category:Methylating agents]]
[[Category:Methyl compounds]]

Latest revision as of 08:55, 2 September 2024

Methyldiazonium
Names
IUPAC name
Methyldiazynium
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/CH3N2/c1-3-2/h1H3/q+1
    Key: RRJZCACJJKZDNV-UHFFFAOYSA-N
  • C[N+]#N
Properties
CH3N2+
Molar mass 43.048 g·mol−1
Acidity (pKa) <10
Conjugate base Diazomethane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

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

[edit]
  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. PMID 17691089.
  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.