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The influence of halogen type on structural features of compounds containing α-halo-α,α-dinitroethyl moieties

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Chemistry of Heterocyclic Compounds Aims and scope

We report the synthesis, as well as the molecular and crystal structures of N-(2-halo-2,2-dinitroethyl)pyrrolidine-2,5-diones (Hal = F, Cl, Br). A combination of X-ray structural analysis and quantum chemistry calculations was used for comparative analysis of molecular packing in the crystals of the synthesized compounds. It was shown that the fluorinated derivative contained a shortened F···F halogen bond of the first type, and in the bromo derivative the bromine atoms formed a relatively strong Br···O=C halogen bond of the second type, while the chlorine atom in the structure of chloro derivative interacted with a nitro group oxygen atom, also forming a weak Cl···O2N halogen bond of the second type. These variations in the “preferences” of different halogen atoms resulted in observable differences in the crystal structures of the studied compounds.

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This work received financial support from the Russian Science Foundation (project RNF 16-13-10404).

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow, 119991, Russia

    Artem O. Dmitrienko, Valentina A. Karnoukhova & Kirill Yu. Suponitsky

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Aleksandr A. Potemkin & Marina I. Struchkova

  3. M. I. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Aleksandr A. Potemkin

  4. Analytika Ltd., 2/1 Serebryakova proezd, Moscow, 129343, Russia

    Irina A. Kryazhevskikh

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  1. Artem O. Dmitrienko
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  2. Valentina A. Karnoukhova
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  3. Aleksandr A. Potemkin
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  4. Marina I. Struchkova
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  6. Kirill Yu. Suponitsky
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Correspondence to Kirill Yu. Suponitsky.

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The Supplementary information file containing data from quantum-chemical calculations and X-ray structural analysis of compounds 2–4 is available from the journal website at http://link.springer.com/journal/10593.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(5), 532–539

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Dmitrienko, A.O., Karnoukhova, V.A., Potemkin, A.A. et al. The influence of halogen type on structural features of compounds containing α-halo-α,α-dinitroethyl moieties. Chem Heterocycl Comp 53, 532–539 (2017). https://doi.org/10.1007/s10593-017-2088-7

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