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 ... View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2003-06

AUTHORS

Yurii A. Simonov, Marina S. Fonarı, Janusz Lipkowski, Arkadii A. Yavolovskii, Eduard V. Ganin

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. More... »

PAGES

27-36

References to SciGraph publications

  • 1996-12. Antimony(III) fluoride: inclusion complexes with crown ethers in JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
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    http://scigraph.springernature.com/pub.10.1023/a:1025612912040

    DOI

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