Methyldiazonium: Difference between revisions

Methyldiazonium
Names
	IUPAC name Methyldiazynium
Identifiers
CAS Number	20404-06-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:176914;
ChEMBL	ChEMBL2419248;
ChemSpider	103148;
KEGG	C20302;
PubChem CID	115287;
UNII	4MD529UV3B;
CompTox Dashboard (EPA)	DTXSID40174355 ;
	InChI InChI=1S/CH3N2/c1-3-2/h1H3/q+1 Key: RRJZCACJJKZDNV-UHFFFAOYSA-N;
	SMILES C[N+]#N;
Properties
Chemical formula	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). Infobox references

Browse history interactively

← Previous edit

Content deleted Content added

VisualWikitext

Inline

Latest revision as of 08:55, 2 September 2024

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 pK_a<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 pK_a 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.

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

[1] Fei, Na; Sauter, Basilius; Gillingham, Dennis (2016). "The pK_a 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.

[Tricker-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.

[1]

[2]

[3]

@@ Line 1: / Line 1: @@
+{{Chembox
-'''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 }}</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>
+<!-- Images -->| ImageFile      = Methyldiazonium.png
+| ImageCaption =
+| OtherNames   =
+| IUPACName    = Methyldiazynium
+| Section1     = {{Chembox Identifiers
+| CASNo = 20404-06-2
+| ChEBI = 176914
+| ChEMBL = 2419248
+| ChemSpiderID = 103148
+| KEGG = C20302
+| PubChem = 115287
+| UNII = 4MD529UV3B
+| StdInChI=1S/CH3N2/c1-3-2/h1H3/q+1
+| StdInChIKey = RRJZCACJJKZDNV-UHFFFAOYSA-N
+| SMILES = C[N+]#N
+ }}
+| Section2 = {{Chembox Properties
+|C=1|H=3|N=2|Formula_Charge=+
+|pKa = <10
+|ConjugateBase = [[Diazomethane]]
+ }}
+}}
+'''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|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>
+:[[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 ==
@@ Line 8: / Line 37: @@
 [[Category:Diazo compounds]]
-[[Category:Carbocations]]
+[[Category:Cations]]
 [[Category:Methylating agents]]
+[[Category:Methyl compounds]]