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1,1,4,4-Tetranitrobutane-2,3-diol and its derivatives. 1. Reaction of dinitromethane potassium salt with glyoxal. Crystal structure of 1,1,4,4-tetranitrobutane-2,3-diol and its diacetate

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

The synthesis of 1,1,4,4-tetranitrobutane-2,3-diol has been carried out via the reaction of the dinitromethane potassium salt with glyoxal, at pH values of 7–8 after reagent mixing and 5.5 at the end of the reaction, in the temperature range 35–37°C. X-ray crystal structure analysis has been performed on 1,1,4,4-tetranitrobutane-2,3-diol and its diacetate. The conformations of these molecules are stabilized to a significant extent by O−...N+-type electrostatic interaction, which was confirmed by quantum-mechanical calculations on 2,2-dinitroethanol as a model molecule.

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Authors and Affiliations

  1. N. N. Semenov Institute of Chemical Physics Branch, Academy of Sciences of the USSR, Chernogolovka

    B. S. Fedorov, N. I. Golovina, L. S. Barinova, R. F. Trofimova, V. V. Arakcheeva & L. O. Atovmyan

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  1. B. S. Fedorov
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  2. N. I. Golovina
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  3. L. S. Barinova
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  4. R. F. Trofimova
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  5. V. V. Arakcheeva
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  6. L. O. Atovmyan
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 830–834, April, 1991.

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Fedorov, B.S., Golovina, N.I., Barinova, L.S. et al. 1,1,4,4-Tetranitrobutane-2,3-diol and its derivatives. 1. Reaction of dinitromethane potassium salt with glyoxal. Crystal structure of 1,1,4,4-tetranitrobutane-2,3-diol and its diacetate. Russ Chem Bull 40, 728–732 (1991). https://doi.org/10.1007/BF00958562

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  • DOI: https://doi.org/10.1007/BF00958562

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