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Supramolecular Structure and Hydrogen Bonding of N,N′-Bis(trifluoromethylsulfonyl)amides of Dicarboxylic Acids

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Abstract

Quantum-chemical DFT simulation of N,N’-bis(trifluoromethylsulfonyl)amides of dicarboxylic acids TfNHСO(CH2)nCONHTf (n = 0–3) has allowed evaluation of their ability to form intramolecular NH···О=C or NH···О=S hydrogen bonds depending on the length of the carbon chain (CH2)n. Self-associates forming the supramolecular structure in the gas phase have been cyclic dimers with intermolecular NH···О=C or NH···О=S hydrogen bonds, containing no intramolecular H-bonds. According to IR spectroscopy data, the compounds with n = 3, 4 have formed self-associates with the NH···О=C bonds in the solid state.

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Funding

This study was financially supported by the Russian Science Foundation (grant 22-13-00036, spectral studies) and performed using the equipment of Baikal Analytical Center for Collective Usage, Siberian Branch, RAS.

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Authors and Affiliations

  1. A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033, Irkutsk, Russia

    N. N. Chipanina, L. L. Tolstikova & B. A. Shainyan

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  1. N. N. Chipanina
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  2. L. L. Tolstikova
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  3. B. A. Shainyan
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Correspondence to B. A. Shainyan.

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B. A. Shainyan is a member of Editorial Board of the Russian Journal of General Chemistry. Other authors declare that they have no conflicts of interest.

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Chipanina, N.N., Tolstikova, L.L. & Shainyan, B.A. Supramolecular Structure and Hydrogen Bonding of N,N′-Bis(trifluoromethylsulfonyl)amides of Dicarboxylic Acids. Russ J Gen Chem 92, 1437–1442 (2022). https://doi.org/10.1134/S1070363222080102

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