Abstract
The title compound, C4H9N5O2+·SO4 2−·H2O, is the monohydrate of the commercially available compound `C4H7N5O·H2SO4·xH2O'. It is obtained by reprecipitation of C4H7N5O·H2SO4·xH2O from dilute sodium hydroxide solution with dilute sulfuric acid. The crystal structure of anhydrous 2,4,5-triamino-1,6-dihydropyrimidin-6-one sulfate is known, although called by the authors 5-amminium-6-amino-isocytosinium sulfate [Bieri et al. (1993). Private communication (refcode HACDEU). CCDC, Cambridge, England]. In the structure, the sulfate group is deprotonated, whereas one of the amino groups is protonated (R 2C—NH3 +) and one is rearranged to a protonated imine group (R 2C=NH2 +). This arrangement is very similar to the known crystal structure of the anhydrate. Several tautomeric forms of the investigated molecule are possible, which leads to questionable proton attributions. The measured data allowed the location of all hydrogen atoms from the residual electron density. In the crystal, ions and water molecules are linked into a three-dimensional network by N—H...O and O—H...O hydrogen bonds.
Highlights
The title compound, C4H9N5O2+ÁSO42ÀÁH2O, is the monohydrate of the commercially available compound ‘C4H7N5OÁH2SO4ÁxH2O’
The sulfate group is deprotonated, whereas one of the amino groups is protonated (R2C—NH3+) and one is rearranged to a protonated imine group (R2C NH2+). This arrangement is very similar to the known crystal structure of the anhydrate
Ions and water molecules are linked into a three-dimensional network by N—HÁ Á ÁO and O—HÁ Á ÁO hydrogen bonds
Summary
2,4,5-Triamino-1,6-dihydropyrimidin-6-one ( called 2,4,5-triamino-6-hydroxypyrimidine sulfate) and/or its tautomer 2,4,5-triamino-6-hydroxypyrimidine are relevant starting materials for either very basic (Traube, 1900) or more advanced organic syntheses, including natural materials such as butterfly-wing pigments (Purrmann, 1940) and potential novel antiviral lead structures (Abbas et al, 2017). The structure of the monohydrate form is elucidated and confirms the protonation of the known structure (CSD refcode: HACDEU; Bieri et al, 1993). The title compound crystallizes in the triclinic space group P1.
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