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Preparation and X-Ray Study of Inclusion Complexes of (4Z,5E)-Pyrimidine-2,4,5,6(1 H,3H)-Tetraone 4,5-Dioxime and the Product of Its Cyclization, (1,2,5)-Oxadiazolo(3,4-d)-Pyrimidine-5,7(4 H,6H)-Dione with Two 18-Membered Macrocycles

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Abstract

The novel dioxime, (4Z,5E)-pyrimidine-2,4,5,6(1H,3H)-tetraone 4,5-dioxime (H2-PTD) was obtained by the interaction of 6-amino-5-nitrosopyrimidine-2,4(1H,3H)-dione with hydroxylamine hydrochloride. X-ray structural analysis determined the 4Z,5E-configuration of the corresponding monoanion, pyrimidine-2,6(1H,3H)-dione-4-iminole-5-iminolate in the inclusion complexes with diazonia-18-crown-6 (1,4,10,13-tetraoxa-7,16-diazoniacyclooctadecane) (H2-DA18C6)2+ (complex (1), stoichiometry 2 : 1), and its ammonium salt in the complex with the cis-syn-cis isomer of dicyclohexano-18-crown-6(DCHA) (cis-syn-cis-2,5,8,15,18,21-hexaoxatricyclo (20.4.0.09,14)hexacosane) (complex (2), stoichiometry 1 : 1). X-ray data were also obtained for the complex of the product of (H2-PTD) cyclization, (1,2,5)-oxadiazolo(3,4-d)pyrimidine-5,7(4H,6H)-dione (OPD) with diaqua diaza-18-crown-6 (complex (3), stoichiometry 2 : 2 : 1).

In (1) the (H-PTD)- anions are joined into dimers through the bifurcated OH...N and OH...O hydrogen bonds and alternate with diazonia-18-crown-6 cations in the chains sustained by the NH(crown) ... O and NH(crown) ...N interactions. The chains are further combined into the 3D network via NH...O(crown) hydrogen bonds. In (2) the self-complementarity of the (H-PTD)- anions facilitates their assembly into the chain via OH...N, NH...O and OH...O interactions. The ammonium cations bridge each anion and the DCHA macrocycle with the formation of a ribbon developed along the [101] direction in the unit cell. Ternary complex (3) is built of the neutral species, diaza-18-crown-6, water molecules and dimers of OPD alternated in the chains and held together by OH...O and NH...O hydrogen bonds.

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Authors and Affiliations

  1. Institute of Applied Physics Academy of Sciences of Moldova, Academy str., 5, MD 2028, Chisinau, Moldova

    Yurii A. Simonov & Marina S. Fonarı

  2. Institute of Physical Chemistry Polish Academy of Sciences Warsaw, Poland

    Janusz Lipkowski

  3. Bogatsky Physico-Chemical Institute of the National Academy of Science of Ukraine, Odessa, Ukraine

    Arkadii A. Yavolovskii

  4. Odessa State Environmental University of the Ministry of Education and Science of, Ukraine

    Eduard V. Ganin

Authors
  1. Yurii A. Simonov
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  2. Marina S. Fonarı
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  5. Eduard V. Ganin
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Correspondence to Marina S. Fonarı.

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Simonov, Y.A., Fonarı, M.S., Lipkowski, J. et al. Preparation and X-Ray Study of Inclusion Complexes of (4Z,5E)-Pyrimidine-2,4,5,6(1 H,3H)-Tetraone 4,5-Dioxime and the Product of Its Cyclization, (1,2,5)-Oxadiazolo(3,4-d)-Pyrimidine-5,7(4 H,6H)-Dione with Two 18-Membered Macrocycles. Journal of Inclusion Phenomena 46, 27–36 (2003). https://doi.org/10.1023/A:1025612912040

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