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Diorganyl dichalcogenides with intramolecular coordination interactions: the synthesis and structure of bis(4,6-dimethylpyrimidin-2-yl) diselenide

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Abstract

Bis(4,6-dimethylpyrimidin-2-yl) diselenide, a new representative of dihetaryl diselenides, was obtained by successively treating selenourea with hydrochloric acid, acetylacetone, potassium hydroxide, and the system iodine—potassium iodide. The unusual planar trans-conformation of this compound (X-ray diffraction data) is stabilized by intramolecular attractive nonvalent Se…N interactions (Se…N, 2.926(1) Å) and stacking of the π-systems of the aromatic heterocycles (the centers of the pyrimidine rings are spaced apart at 3.365(2) Å). The energy parameters of the factors that make the molecular structure flattened were estimated by quantum chemical DFT calculations.

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Authors and Affiliations

  1. R. E. Alekseev Nizhny Novgorod State Technical University, 24 ul. Minina, 603950, Nizhny Novgorod, Russian Federation

    A. V. Borisov, Zh. V. Matsulevich, V. K. Osmanov & G. N. Borisova

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

    A. O. Chizhov

  3. Baku State University, 23 ul. Z. Khalilova, AZ 1148, Baku, Republic of Azerbaijan

    G. Z. Mammadova & A. M. Maharramov

  4. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    R. R. Aisin & V. N. Khrustalev

Authors
  1. A. V. Borisov
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  2. Zh. V. Matsulevich
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  3. V. K. Osmanov
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  4. G. N. Borisova
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  5. A. O. Chizhov
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  6. G. Z. Mammadova
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  7. A. M. Maharramov
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  8. R. R. Aisin
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  9. V. N. Khrustalev
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Correspondence to A. V. Borisov.

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Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2462–2466, Novemer, 2013.

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Borisov, A.V., Matsulevich, Z.V., Osmanov, V.K. et al. Diorganyl dichalcogenides with intramolecular coordination interactions: the synthesis and structure of bis(4,6-dimethylpyrimidin-2-yl) diselenide. Russ Chem Bull 62, 2462–2466 (2013). https://doi.org/10.1007/s11172-013-0356-y

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  • DOI: https://doi.org/10.1007/s11172-013-0356-y

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