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Orientation of hydrogen bond in H-complexes of sulfones and sulfonamides

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Abstract

According to the data of quantum chemical calculations using the DFT method (B3LYP/6-311G*), dimethylsulfone (I), N,N-dimethylmethanesulfonamide (II) and N,N-dimethyltrifluoromethanesulfonamide (III) form with methanol and phenol H-complexes of two types: (1) having nonlinear structure and (2) bidentate complexes with participation of both oxygen atom lone pairs in the formation of the H-bond. The angle determining the directionality of the hydrogen bond with respect to the axis of the nearest lone electron pair of the SO2 group oxygen atom in the conformational isomers of these complexes falls within the range 3°–100°. Variation of the calculated values of Δν(OH) in the H-complexes is parallel to that observed in their IR spectra and reflects the decrease of basicity of the sulfonyl group in the order I > II > III.

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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

    L. P. Oznobikhina, N. N. Chipanina, T. N. Aksamentova & B. A. Shainyan

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  1. L. P. Oznobikhina
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  2. N. N. Chipanina
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  3. T. N. Aksamentova
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  4. B. A. Shainyan
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Correspondence to B. A. Shainyan.

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Original Russian Text © L.P. Oznobikhina, N.N. Chipanina, T.N. Aksamentova, B.A. Shainyan, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 9, No. 8, pp. 1314–1322.

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Oznobikhina, L.P., Chipanina, N.N., Aksamentova, T.N. et al. Orientation of hydrogen bond in H-complexes of sulfones and sulfonamides. Russ J Gen Chem 79, 1674–1682 (2009). https://doi.org/10.1134/S1070363209080167

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  • DOI: https://doi.org/10.1134/S1070363209080167

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