Interaction of acetonitrile with trifluoromethanesulfonic acid: unexpected formation of a wide variety of structuresElectronic supplementary information (ESI) available: Tables and spectra. See DOI: 10.1039/c2ob06841a
Interaction of acetonitrile with trifluoromethanesulfonic acid has been studied by multinuclear NMR and ESI-MS. It has been found that the interaction results in formation of a great variety of different cations and neutral compounds which is controlled by the ratio of CH 3 CN to TfOH. In the presen...
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Format | Journal Article |
Language | English |
Published |
23.02.2012
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Abstract | Interaction of acetonitrile with trifluoromethanesulfonic acid has been studied by multinuclear NMR and ESI-MS. It has been found that the interaction results in formation of a great variety of different cations and neutral compounds which is controlled by the ratio of CH
3
CN to TfOH. In the presence of an excess of the acid (molar ratio 1:814) diprotonated
N
-acetylacetamidine
1
is formed as the major product, which eventually transforms into protonated acetamidine
3
and acetic acid
4
. At molar ratio of (1:12) diprotonated 2,4-dimethyl-6-methylidene-3
H
-1,3,5-triazine
12
, tautomer of the diprotonated trimethyl-s-triazine
11
, becomes the main product at an early stage of the reaction and diprotonated 1-(dimethyl-1,3,5-triazin-2-yl)prop-1-en-2-ol
15
at a later stage. In the case of a large excess of acetonitrile (420:1) trication
17
is formed as a result of the interaction between
11
and
12
along with some oligomers [(CH
3
CN)
3
]
n
(
n
= 412).
Interaction of the two simple compounds, CH
3
CN and TfOH, results in formation of a variety of complicated structures, the composition of the reaction products being a function of the ratio of CH
3
CN to TfOH. |
---|---|
AbstractList | Interaction of acetonitrile with trifluoromethanesulfonic acid has been studied by multinuclear NMR and ESI-MS. It has been found that the interaction results in formation of a great variety of different cations and neutral compounds which is controlled by the ratio of CH
3
CN to TfOH. In the presence of an excess of the acid (molar ratio 1:814) diprotonated
N
-acetylacetamidine
1
is formed as the major product, which eventually transforms into protonated acetamidine
3
and acetic acid
4
. At molar ratio of (1:12) diprotonated 2,4-dimethyl-6-methylidene-3
H
-1,3,5-triazine
12
, tautomer of the diprotonated trimethyl-s-triazine
11
, becomes the main product at an early stage of the reaction and diprotonated 1-(dimethyl-1,3,5-triazin-2-yl)prop-1-en-2-ol
15
at a later stage. In the case of a large excess of acetonitrile (420:1) trication
17
is formed as a result of the interaction between
11
and
12
along with some oligomers [(CH
3
CN)
3
]
n
(
n
= 412).
Interaction of the two simple compounds, CH
3
CN and TfOH, results in formation of a variety of complicated structures, the composition of the reaction products being a function of the ratio of CH
3
CN to TfOH. |
Author | Vasiliev, Vladimir G Genaev, Alexander M Shubin, Vyacheslav G Salnikov, George E |
AuthorAffiliation | Vorozhtsov Novosibirsk Institute of Organic Chemistry |
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Notes | 10.1039/c2ob06841a Electronic supplementary information (ESI) available: Tables and spectra. See DOI |
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Title | Interaction of acetonitrile with trifluoromethanesulfonic acid: unexpected formation of a wide variety of structuresElectronic supplementary information (ESI) available: Tables and spectra. See DOI: 10.1039/c2ob06841a |
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