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Issue 11, 2012
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Interaction of acetonitrile with trifluoromethanesulfonic acid: unexpected formation of a wide variety of structures

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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 CH3CN to TfOH. In the presence of an excess of the acid (molar ratio 1 : 8–14) 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 : 1–2) diprotonated 2,4-dimethyl-6-methylidene-3H-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 (4–20 : 1) trication 17 is formed as a result of the interaction between 11 and 12 along with some oligomers [(CH3CN)3]n (n = 4–12).

Graphical abstract: Interaction of acetonitrile with trifluoromethanesulfonic acid: unexpected formation of a wide variety of structures

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Publication details

The article was received on 02 Nov 2011, accepted on 05 Jan 2012 and first published on 06 Jan 2012


Article type: Paper
DOI: 10.1039/C2OB06841A
Org. Biomol. Chem., 2012,10, 2282-2288

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    Interaction of acetonitrile with trifluoromethanesulfonic acid: unexpected formation of a wide variety of structures

    G. E. Salnikov, A. M. Genaev, V. G. Vasiliev and V. G. Shubin, Org. Biomol. Chem., 2012, 10, 2282
    DOI: 10.1039/C2OB06841A

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