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Five pseudopolymorphs of 6-amino-2-thiouracil: absence of N-H...S hydrogen bonds. 2013

Wilhelm Maximilian Hützler, and Michael Bolte
Institut für Organische Chemie und Chemische Biologie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany.

In order to study the preferred hydrogen-bonding pattern of 6-amino-2-thiouracil, C(4)H(5)N(3)OS, (I), crystallization experiments yielded five different pseudopolymorphs of (I), namely the dimethylformamide disolvate, C(4)H(5)N(3)OS·2C(3)H(7)NO, (Ia), the dimethylacetamide monosolvate, C(4)H(5)N(3)OS·C(4)H(9)NO, (Ib), the dimethylacetamide sesquisolvate, C(4)H(5)N(3)OS·1.5C(4)H(9)NO, (Ic), and two different 1-methylpyrrolidin-2-one sesquisolvates, C(4)H(5)N(3)OS·1.5C(5)H(9)NO, (Id) and (Ie). All structures contain R(2)(1)(6) N-H...O hydrogen-bond motifs. In the latter four structures, additional R(2)(2)(8) N-H...O hydrogen-bond motifs are present stabilizing homodimers of (I). No type of hydrogen bond other than N-H...O is observed. According to a search of the Cambridge Structural Database, most 2-thiouracil derivatives form homodimers stabilized by an R(2)(2)(8) hydrogen-bonding pattern, with (i) only N-H...O, (ii) only N-H...S or (iii) alternating pairs of N-H...O and N-H...S hydrogen bonds.

UI MeSH Term Description Entries
D003460 Crystallization The formation of crystalline substances from solutions or melts. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Crystalline Polymorphs,Polymorphism, Crystallization,Crystal Growth,Polymorphic Crystals,Crystal, Polymorphic,Crystalline Polymorph,Crystallization Polymorphism,Crystallization Polymorphisms,Crystals, Polymorphic,Growth, Crystal,Polymorph, Crystalline,Polymorphic Crystal,Polymorphisms, Crystallization,Polymorphs, Crystalline
D006860 Hydrogen Bonding A low-energy attractive force between hydrogen and another element. It plays a major role in determining the properties of water, proteins, and other compounds. Hydrogen Bonds,Bond, Hydrogen,Hydrogen Bond
D013889 Thiouracil Occurs in seeds of Brassica and Crucifera species. Thiouracil has been used as antithyroid, coronary vasodilator, and in congestive heart failure although its use has been largely supplanted by other drugs. It is known to cause blood dyscrasias and suspected of terato- and carcinogenesis.
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D018360 Crystallography, X-Ray The study of crystal structure using X-RAY DIFFRACTION techniques. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) X-Ray Crystallography,Crystallography, X Ray,Crystallography, Xray,X Ray Crystallography,Xray Crystallography,Crystallographies, X Ray,X Ray Crystallographies

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