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MOLECULAR STRUCTURES AND CRYSTAL PACKINGS OF STYRYLDIAZINES

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Abstract

Crystal structures of three isomeric styryldiazine derivatives (E)-2-(3,4-dimetoxystryl)pyrazine, (E)-2-(3,4-dimetoxystryl)pyrimidine, and (E)-4-(3,4-dimetoxystryl)pyrimidine with different positions of nitrogen atoms are studied. These compounds can be used as potential initial compounds for biologically active (antibacterial or antitumor) agents, pesticides, fungicides, dyes, analytical reagents. Even though these molecules have similar chemical structures and geometric parameters in the crystal, the crystal packing motifs of these three compounds differ significantly. The conducted PBE0/6-31G(d,p) quantum chemical calculations show that these molecules may have several conformers with close energies, including those observed in the crystal, and that these forms may transform into each other through barriers not exceeding 43.5 kJ/mol. The highest density at 120 K and the highest energy of crystal lattice calculated by the UNI force field are observed for the pyrimidine derivative (E)-2-(3,4-dimetoxystryl)pyrimidine (6). This is the only structure that exhibits photocyclization in solid state due to the fact that its crystal contains centrosymmetric dimers with a distance between the atoms of olefin fragments equal to ≈ 3.9 Å.

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Funding

The reported study was funded by RFBR, project number 19-33-90227. The structures were determined with the support of the Ministry of Science and Higher Education of the Russian Federation using the equipment of the Center for the Study of Molecular Structures INEOS RAS. The quantum chemical calculations were performed using resources of the Siberian Supercomputing Centre of ICMMG SB RAS.

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Authors and Affiliations

  1. Mendeleev University of Chemical Technology of Russia, Moscow, Russia

    A. E. Saifutiarova, O. A. Fedorova & I. V. Fedyanin

  2. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia

    A. E. Saifutiarova, V. A. Karnoukhova, E. N. Gulakova, O. A. Fedorova & I. V. Fedyanin

  3. Plekhanov Russian University of Economics, Moscow, Russia

    I. V. Fedyanin

Authors
  1. A. E. Saifutiarova
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  2. V. A. Karnoukhova
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  3. E. N. Gulakova
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  4. O. A. Fedorova
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  5. I. V. Fedyanin
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Correspondence to A. E. Saifutiarova.

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The authors declare that they have no conflict of interests.

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Russian Text © The Author(s), 2021, published in Zhurnal Strukturnoi Khimii, 2021, Vol. 62, No. 4, pp. 565-574.https://doi.org/10.26902/JSC_id71040

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Saifutiarova, A.E., Karnoukhova, V.A., Gulakova, E.N. et al. MOLECULAR STRUCTURES AND CRYSTAL PACKINGS OF STYRYLDIAZINES. J Struct Chem 62, 527–536 (2021). https://doi.org/10.1134/S002247662104003X

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  • DOI: https://doi.org/10.1134/S002247662104003X

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