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Experimental and theoretical investigation of self-association in inert environment of new triflamide derivatives

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Abstract

According to the data of IR spectroscopy and quantum chemical calculations N-(2-phenylethyl) trifluoromethanesulfonamide exists in an inert solvent CCl4 as an equilibrium mixture of the monomer and chain associates; in contrast, N-(5-iodocyclopentenyl)-1,1,1-trifluoromethanesulfonamide under the same conditions is prone to the formation of cyclic self-associates. The behavior of N,N′-(cyclohexenediyl)-bis(1,1,1-trifluoromethane sulfonamide) in the same medium is far more complicated: apart from the monomer with intramolecular hydrogen bonds (HB), it forms only cyclic self-associates with eight-membered and eleven-membered rings.

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Authors and Affiliations

  1. Irkutsk Faworsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, 664033, Russia

    I. V. Sterkhova, M. Yu. Moskalik & B. A. Shainyan

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  1. I. V. Sterkhova
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  2. M. Yu. Moskalik
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  3. B. A. Shainyan
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Correspondence to I. V. Sterkhova.

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Original English Text © I.V. Sterkhova, M.Yu. Moskalik, B.A. Shainyan, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 11, pp. 1617–1622.

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Sterkhova, I.V., Moskalik, M.Y. & Shainyan, B.A. Experimental and theoretical investigation of self-association in inert environment of new triflamide derivatives. Russ J Org Chem 49, 1594–1599 (2013). https://doi.org/10.1134/S1070428013110055

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  • DOI: https://doi.org/10.1134/S1070428013110055

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