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Solvatochromism of heteroaromatic compounds: XXX. N-Methyltrifluoromethanesulfonamide as hydrogen-bond donor

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Abstract

In two-centered H-complexes with protophilic solvents, the monomer of N-methyltrifluoromethanesulfonamide I behaves as a strong H-bond donor, stronger than 4-fluorophenol and ranking second after 4-nitrophenol. In protophilic media, amide I exists as monomeric H-complexes with a two-centered H-bond and 1:2 H-complexes of the open-chair dimer with a bifurcated (three-centered) hydrogen bond. The formation of a strong bifurcated H-bond weaken the bridging N-H.‥O=S bond.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    I. V. Sterkhova, N. N. Chipanina, B. A. Shainyan & V. K. Turchaninov

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  1. I. V. Sterkhova
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  2. N. N. Chipanina
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  3. B. A. Shainyan
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  4. V. K. Turchaninov
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Original Russian Text © I.V. Sterkhova, N.N. Chipanina, B.A. Shainyan, V.K. Turchaninov, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77, No. 1, pp. 90–96.

For communication XXIX, see [1].

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Sterkhova, I.V., Chipanina, N.N., Shainyan, B.A. et al. Solvatochromism of heteroaromatic compounds: XXX. N-Methyltrifluoromethanesulfonamide as hydrogen-bond donor. Russ J Gen Chem 77, 84–89 (2007). https://doi.org/10.1134/S1070363207010112

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  • DOI: https://doi.org/10.1134/S1070363207010112

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