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Structure of benzo- and dibenzocrown ethers and their H-bonded adducts. 4. Structural motifs in the 2,4-dithiouracil complexes with 4-bromo- and 4-nitrobenzo-18-crown-6, [2.4]dibenzo- and thia[1.5]dibenzo-18-crown-6

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Abstract

Four novel complexes of 2,4-dithiouracil (pyrimidine-2,4(1H,3H)-dithione, DTU) with 18-membered benzo- and dibenzo-crown ethers were synthesized in approximately the same conditions and studied by single crystal diffraction. Hydrogen bonding was observed to be the most important for the complexation in the solid state but π–π interactions also contribute to it. The crystalline monohydrates of the 1:1:1 stoichiometry are recorded for 4-bromo- and 4-nitrobenzo-18-crown-6 (complexes 1 and 2), while complexes with [2.4]dibenzo- and thia[1.5]dibenzo-18-crown-6 (complexes 3 and 4) represent anhydrous adducts of the 2:2 ratio. The crystal structures reveal three supramolecular structural motifs: the alternative chain for the ternary complex 1 and two types of capsules for complexes 2−4 where the DTU dimers are encapsulated inside the space restricted by two crown molecules.

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Authors and Affiliations

  1. Institute of Applied Physics, Academy of Sciences of Moldova, Academy str., 5, MD2028, Chisinau, Moldova

    Marina S. Fonari & Yurii A. Simonov

  2. IMEM-CNR, Parma, Italy

    Gabriele Bocelli

  3. Odessa State Environmental University, Ministry of Education and Science of Ukraine, Lvovskaya str., 15, 65016, Odessa, Ukraine

    Eduard V. Ganin

  4. Department of Chemistry, Tamkang University, 151 Ying-Chuan Road, Tamsui, Taipei, 25137, Taiwan, ROC

    Wen-Jwu Wang

  5. A.V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, Lustdorfskaya doroga 86, 650080, Odessa, Ukraine

    Sergei M. Pluzhnik-Gladyr, Vyacheslav V. Tkachyuk, Sergei A. Kotlyar & Gerbert L. Kamalov

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  1. Marina S. Fonari
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  2. Yurii A. Simonov
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  3. Gabriele Bocelli
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  4. Eduard V. Ganin
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  5. Wen-Jwu Wang
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  7. Vyacheslav V. Tkachyuk
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  8. Sergei A. Kotlyar
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  9. Gerbert L. Kamalov
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Correspondence to Marina S. Fonari.

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For part 3 see JIPh., 56, 345 (2006).

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Fonari, M.S., Simonov, Y.A., Bocelli, G. et al. Structure of benzo- and dibenzocrown ethers and their H-bonded adducts. 4. Structural motifs in the 2,4-dithiouracil complexes with 4-bromo- and 4-nitrobenzo-18-crown-6, [2.4]dibenzo- and thia[1.5]dibenzo-18-crown-6. J Incl Phenom Macrocycl Chem 61, 367–375 (2008). https://doi.org/10.1007/s10847-008-9431-7

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