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

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

Journal

Organic and Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2012, Volume: 10, Number: 11, Pages: 2282-2288 Pages count : 7 DOI: 10.1039/c2ob06841a

Authors

Salnikov George E. ¹ , Genaev Alexander M. ¹ , Vasiliev Vladimir G. ¹ , Shubin Vyacheslav G. ¹

Affiliations

1	(Данные Web of science) Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

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).

Salnikov G.E. , Genaev A.M. , Vasiliev V.G. , Shubin V.G.
Interaction of acetonitrile with trifluoromethanesulfonic acid: unexpected formation of a wide variety of structures
Organic and Biomolecular Chemistry. 2012. V.10. N11. P.2282-2288. DOI: 10.1039/c2ob06841a WOS Scopus РИНЦ

Web of science	WOS:000300656600015
Scopus	2-s2.0-84857617137
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