Influence of Deuteration and Fluorination on the Supramolecular Architecture of Pyridine N-Oxide Crystals

Authors

  • Prof. Dr. Oleg V. Shishkin,

    Corresponding author
    1. Division of Functional Materials Chemistry, SSI “Institute for Single Crystals”, National Academy of Science of Ukraine, 60 Lenina ave., Kharkiv, 61001 (Ukraine)
    2. Department of Inorganic Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody sq., Kharkiv 61122 (Ukraine)
    • Division of Functional Materials Chemistry, SSI “Institute for Single Crystals”, National Academy of Science of Ukraine, 60 Lenina ave., Kharkiv, 61001 (Ukraine)
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  • Dr. Svitlana V. Shishkina,

    1. Division of Functional Materials Chemistry, SSI “Institute for Single Crystals”, National Academy of Science of Ukraine, 60 Lenina ave., Kharkiv, 61001 (Ukraine)
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  • Prof. Dr. Andrey V. Maleev,

    1. Vladimir State University, 87 Gorky str., Vladimir, 600000 (Russian Federation)
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  • Roman I. Zubatyuk,

    1. Division of Functional Materials Chemistry, SSI “Institute for Single Crystals”, National Academy of Science of Ukraine, 60 Lenina ave., Kharkiv, 61001 (Ukraine)
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  • Dr. Vera Vasylyeva,

    1. Inorganic Chemistry I, Ruhr-University Bochum, Universitaetstrasse 150, 44801 Bochum (Germany)
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  • Dr. Klaus Merz

    Corresponding author
    1. Inorganic Chemistry I, Ruhr-University Bochum, Universitaetstrasse 150, 44801 Bochum (Germany)
    • Inorganic Chemistry I, Ruhr-University Bochum, Universitaetstrasse 150, 44801 Bochum (Germany)
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Abstract

To understand how deuterium and fluorine substituents influence the supramolecular architecture of pyridine N-oxide crystals, the crystal structure of 3-fluoropyridine N-oxide (PNO-3F) was determined and the crystal packing motives of non-deuterated pyridine-N-oxide (PNO), partial-deuterated pyridine-N-oxide (PNO-D) and PNO-3F were analyzed based on ab initio quantum-chemical calculations of the intermolecular interaction energy, using the MP2/6-311G(d,p) method. The appearance of the weak-directing substituents deuterium and fluorine leads to significant changes in the crystal organization of the isotropic packing of PNO molecules.

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