Several aspects of intermolecular interactions between the carbonyl and imine groups in the crystals of compounds containing six-membered heterocycles

Головина, Н. И.; Nechiporenko, G. N.; Zyuzin, I. N.; Лемперт, Д. Б.; Nemtsev, G. G.; Шилов, Г. В.; Утенышев, А. Н.; Bozhenko, K. V.

doi:10.1007/s10947-008-0156-7

Cited by 5 publications

(4 citation statements)

References 3 publications

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“…A Cambridge Structural Database (CSD, Version 5.34 of 2012, plus two updates; Allen, 2002) search was performed for 6-aminouracil and yielded three structures, viz. one solventfree 6-aminouracil (CSD refcode COTVIR; Golovina et al, 2008), one 6-aminouracil monohydrate (COTVOX; Golovina et al, 2008) and one cocrystal with 5-fluorocytosine (MECVIB; Tutughamiarso et al, 2012).…”

Section: Tablementioning

confidence: 99%

Three new pseudopolymorphs of 6-aminouracil

Gerhardt

Bolte

2013

Acta Crystallogr C

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Since 6-aminouracil derivatives show diversified use in various fields of application, we crystallized 6-aminouracil to examine its preferred hydrogen-bonding frameworks. 6-Aminouracil shows two rigid hydrogen-bonding sites, viz. one acceptor-donor-acceptor (ADA) site and one donor-donor-acceptor (DDA) site. During various crystallization attempts, we obtained three structures, namely two dimethylacetamide monosolvates, C4H5N3O2·C4H9NO, and a 1-methylpyrrolidin-2-one monosolvate, C4H5N3O2·C5H9NO. In all three structures, R2(1)(6) N-H...O hydrogen-bonding patterns link the molecules to their respective solvent molecules. The formation of R2(2)(8) N-H...O hydrogen-bond motifs between 6-aminouracil molecules can only be found in two-dimensional frameworks, whereas R3(3)(14) N-H...O patterns are present when zigzag chzins of 6-aminouracil molecules are formed.

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Section: Tablementioning

confidence: 99%

Three new pseudopolymorphs of 6-aminouracil

Gerhardt

Bolte

2013

Acta Crystallogr C

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“…In addition to dim9, R 2 2 (8) homodimers of 5-FC (dim2) and of 6-aminouracil (dim10) each characterized by two N-HÁ Á ÁO hydrogen bonds are observed in (IV). Similar interactions are also found in the monohydrate structure of 5-FC [refcode BIRMEU03 (Hulme & Tocher, 2006)] and in the solvent-free structure of 6aminouracil [refcode COTVIR (Golovina et al, 2008)]. The energy released during the formation of dim2 and dim10 (101.1 kJ mol À1 for dim2 and 57.8 kJ mol À1 for dim10) might be sufficient to compensate the energy difference of 57.3 kJ mol À1 between dim8 and dim9.…”

Section: Table 15mentioning

confidence: 61%

Cocrystals of 5-fluorocytosine. I. Coformers with fixed hydrogen-bonding sites

Tutughamiarso¹,

Wagner²,

Egert³

2012

Acta Crystallogr B Struct Sci

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The antifungal drug 5-fluorocytosine (4-amino-5-fluoro-1,2-dihydropyrimidin-2-one) was cocrystallized with five complementary compounds in order to better understand its drug-receptor interaction. The first two compounds, 2-aminopyrimidine (2-amino-1,3-diazine) and N-acetylcreatinine (N-acetyl-2-amino-1-methyl-5H-imidazol-4-one), exhibit donor-acceptor sites for R(2)(2)(8) heterodimer formation with 5-fluorocytosine. Such a heterodimer is observed in the cocrystal with 2-aminopyrimidine (I); in contrast, 5-fluorocytosine and N-acetylcreatinine [which forms homodimers in its crystal structure (II)] are connected only by a single hydrogen bond in (III). The other three compounds 6-aminouracil (6-amino-2,4-pyrimidinediol), 6-aminoisocytosine (2,6-diamino-3H-pyrimidin-4-one) and acyclovir [acycloguanosine or 2-amino-9-[(2-hydroxyethoxy)methyl]-1,9-dihydro-6H-purin-6-one] possess donor-donor-acceptor sites; therefore, they can interact with 5-fluorocytosine to form a heterodimer linked by three hydrogen bonds. In the cocrystals with 6-aminoisocytosine (Va)-(Vd), as well as in the cocrystal with the antiviral drug acyclovir (VII), the desired heterodimers are observed. However, they are not formed in the cocrystal with 6-aminouracil (IV), where the components are connected by two hydrogen bonds. In addition, a solvent-free structure of acyclovir (VI) was obtained. A comparison of the calculated energies released during dimer formation helped to rationalize the preference for hydrogen-bonding interactions in the various cocrystal structures.

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“…The availability of synthetic routes for THICA enables its wide application in practical oxidation. THICA is structurally similar to a reported safe and efficient reagent for chlorination and oxidation, namely trichloroisocyanuric acid [79], and X-ray diffraction has been used to determine the structures of its dihydrate 4-aminouracil and 4-aminouracil monohydrate [80]. The promotional effects of THICA in catalytic oxidation of hydrocarbons have mainly been reported since 2003 by Ishii's group [52].…”

Section: Thica-mediated Aerobic Oxidationmentioning

confidence: 99%