Hydrogen-bonding patterns in 2-amino-4,6-dimethylpyrimidinium hydrogen sulfate

Hemamalini, Madhukar; Muthiah, Packianathan Thomas; Rychłewska, Urszula; Plutecka, Agnieszka

doi:10.1107/s0108270104030975

Cited by 14 publications

(13 citation statements)

References 16 publications

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“…The aminopyrimidinium cations are embedded between these zigzag chains. This type of zigzag supramolecular chain of hydrogen sulfate ions has also been reported in the crystal structures of 2-amino-4,6dimethylpyrimidinium hydrogen sulfate (Hemamalini et al, 2005), 8-hydroxy-5,7-dimethylquinolin-1-ium hydrogen sulfate (Thanigaimani et al, 2013) and anilinium hydrogen sulfate (Boutobba et al, 2010). The three-dimensional supramolecular architecture is shown in Fig.…”

Section: Resultssupporting

confidence: 72%

Supramolecular architectures in cytosinium 6-chloronicotinate monohydrate and 5-bromo-6-methylisocytosinium hydrogen sulfate

et al. 2018

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Aminopyrimidine derivatives are biologically important as they are components of nucleic acids and drugs. The crystals of two new salts, namely cytosinium 6-chloronicotinate monohydrate, CHNO·CHClNO·HO, (I), and 5-bromo-6-methylisocytosinium hydrogen sulfate (or 2-amino-5-bromo-4-oxo-6-methylpyrimidinium hydrogen sulfate), CHBrNO·HSO, (II), have been prepared and characterized by single-crystal X-ray diffraction. The pyrimidine ring of both compounds is protonated at the imine N atom. In hydrated salt (I), the primary R(8) ring motif (supramolecular heterosynthon) is formed via a pair of N-H...O(carboxylate) hydrogen bonds. The cations, anions and water molecule are hydrogen bonded through N-H...O, N-H...N, O-H...O and C-H...O hydrogen bonds, forming R(8), R(7) and R(21) motifs, leading to a hydrogen-bonded supramolecular sheet structure. The supramolecular double sheet structure is formed via water-carboxylate O-H...O hydrogen bonds and π-π interactions between the anions and the cations. In salt (II), the hydrogen sulfate ions are linked via O-H...O hydrogen bonds to generate zigzag chains. The aminopyrimidinium cations are embedded between these zigzag chains. Each hydrogen sulfate ion bridges two cations via pairs of N-H...O hydrogen bonds and vice versa, generating two R(8) ring motifs (supramolecular heterosynthon). The cations also interact with one another via halogen-halogen (Br...Br) and halogen-oxygen (Br...O) interactions.

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Section: Resultssupporting

confidence: 72%

Supramolecular architectures in cytosinium 6-chloronicotinate monohydrate and 5-bromo-6-methylisocytosinium hydrogen sulfate

et al. 2018

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“…We report herein on the synthesis and crystal structure of the title molecular salt. The geometric parameters are comparable with those of similar structures (Moghimi et al, 2004;Hemamalini et al, 2005) The title molecular salt, Fig. 1, contains a 2-amino-1-methyl-5H-imidazolium-4-one cation (protonated at the N atom, N1, in the imidazole unit) and a 4-methylbenzenesulfonate anion (deprotonated at the hydroxyl O atom, O1).…”

Section: Structure Descriptionsupporting

confidence: 64%

2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium 4-methylbenzenesulfonate

2016

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The title molecular salt, C4H8N3O+·C7H7O3S−, is composed of a 2-amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium cation and a 4-methylbenzenesulfonate anion. The cation is protonated at its N atom and the anion is deprotonated at its hydroxy O atom. The imidazole ring is planar (r.m.s. deviation = 0.033 Å) and makes a dihedral angle of 7.87 (10)° with the benzene ring of the anion. In the crystal, the anions and cations are connected by two N—H...O hydrogen bonds, generating anR22(8) ring motif. These units are linked by further N—H...O hydrogen bonds and C—H...O and C—H...π contacts to form chains propagating along thea-axis direction.

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“…The crystal structures of aminopyrimidine derivatives (Schwalbe & Williams, 1982), aminopyrimidine carboxylates (Hu et al, 2002) and co-crystal structures (Chinnakali et al, 1999) have been reported. The crystal structures of 2-amino-4,6-dimethylpyrimidinium bromide 2-amino-4,6-dimethyl-pyrimidine monohydrate (Panneerselvam et al, 2004), 2amino-4,6-dimethylpyrimidinium hydrogen sulfate (Hemamalini et al, 2005) and bis(2,4-diamino-6-oxopyrimidinium) sulfate monohydrate (Muthiah et al, 2004) have been recently reported from our laboratory. Most of the supramolecular crystals originate from strong N-HÁ Á ÁO and O-HÁ Á ÁN hydrogen bonds, and weak C-HÁ Á ÁO bonds are known to play a significant role in determining the molecular packing of organic solids (Taylor & Kennard, 1982).…”

Section: Commentmentioning

confidence: 99%

Hydrogen-bonding patterns in 2-amino-4,6-dimethylpyrimidine–cinnamic acid (1/2)

et al. 2005

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In the title compound, C6H9N3·2C9H8O2, an aminopyrimidine–cinnamic acid 1:2 cocrystal, the 2‐amino‐4,6‐dimethylpyrimidine molecule forms two eight‐membered hydrogen‐bonded rings [R22(8) motif] with the carboxylic acid groups from two independent cinnamic acid molecules via N—H⋯O and O—H⋯N hydrogen bonds. The cinnamic acid molecules are linked by C—H⋯O hydrogen bonds to form chains along two axes.

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Hydrogen-bonding patterns in 2-amino-4,6-dimethylpyrimidinium hydrogen sulfate

Cited by 14 publications

References 16 publications

Supramolecular architectures in cytosinium 6-chloronicotinate monohydrate and 5-bromo-6-methylisocytosinium hydrogen sulfate

Supramolecular architectures in cytosinium 6-chloronicotinate monohydrate and 5-bromo-6-methylisocytosinium hydrogen sulfate

2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium 4-methylbenzenesulfonate

Hydrogen-bonding patterns in 2-amino-4,6-dimethylpyrimidine–cinnamic acid (1/2)

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