2-Amino-4-methoxy-6-methylpyrimidin-1-ium trifluoroacetate

Jeevaraj, Muthaiah; Edison, Bellarmin; Kavitha, Savaridasson Jose; Thanikasalam, Kanagasabapathy; Britto, Sebastian; Balasubramani, Kasthuri

doi:10.1107/s2414314616010105

Cited by 6 publications

(5 citation statements)

References 7 publications

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“…This set of fused rings can be represented by the graph-set notations R 2 2 (8), R 2 4 (8) and R 2 2 (8). This type of motif has been reported previously in the crystal structures of trimethoprim hydrogen glutarate (Robert et al, 2001) and 2-amino-4-methoxy-6-methylpyridinium trifluoroacetate (Jeevaraj et al, 2016). These arrays are further linked via pairwise C-HÁ Á ÁO hydrogen bonds to generate another R 2 2 (8) ring motif as part of a [100] chain (Fig.…”

Section: Supramolecular Featuressupporting

confidence: 68%

Crystal structure and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 2-hydroxybenzoate

et al. 2017

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In the title molecular salt, C 6 H 10 N 3 O + ÁC 7 H 5 O 3 À , the cation is protonated at the N atom lying between the amine and methyl substituents and the dihedral angle between the carboxyl group and its attached ring in the anion is 4.0 (2). The anion features an intramolecular O-HÁ Á ÁO hydrogen bond, which closes an S(6) ring. The cation and anion are linked by two N-HÁ Á ÁO hydrogen bonds [R 2 2 (8) motif] to generate an ion pair in which the dihedral angle between the aromatic rings is 8.34 (9) . Crystal symmetry relates two ion pairs bridged by further N-HÁ Á ÁO hydrogen bonds into a tetrameric DDAA array. The tetramers are linked by pairs of C-HÁ Á ÁO hydrogen bonds to generate [100] chains. Hirshfeld surface and fingerprint plot analyses are presented.

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Section: Supramolecular Featuressupporting

confidence: 68%

Crystal structure and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 2-hydroxybenzoate

et al. 2017

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“…2. The same type of conjoined motif has been reported in the crystal structures of trimethoprim hydrogen glutarate (Robert et al, 2001), 2-amino-4-methoxy-6-methylpyridinium trifluoroacetate (Jeevaraj et al, 2016) and 2-amino-4-methoxy-6-methylpyrimidinium 2-hydroxybenzoate (Jeevaraj et al, 2017).…”

Section: Supramolecular Featuressupporting

confidence: 71%

Supramolecular patterns and Hirshfeld surface analysis in the crystal structure of bis(2-amino-4-methoxy-6-methylpyrimidinium) isophthalate

et al. 2017

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In the title molecular salt, 2C 6 H 10 N 3 O + ÁC 8 H 4 O 4 2À , the N atom of each of the two 2-amino-4-methoxy-6-methylpyrimidine molecules lying between the amine and methyl groups has been protonated. The dihedral angles between the pyrimidine rings of the cations and the benzene ring of the succinate dianion are 5.04 (8) and 7.95 (8) . Each of the cations is linked to the anion through a pair of N-HÁ Á ÁO(carboxylate) hydrogen bonds, forming cyclic R 2 2 (8) ring motifs which are then linked through inversion-related N-HÁ Á ÁO hydrogen bonds, giving a central R 2 4 (8) motif. Peripheral amine N-HÁ Á ÁO hydrogen-bonding interactions on either side of the succinate anion, also through centrosymmetric R 2 2 (8) extensions, form one-dimensional ribbons extending along [211]. The crystal structure also features -stacking interactions between the aromatic rings of the pyrimidine cations [minimum ring centroid separation = 3.6337 (9) Å ]. The intermolecular interactions were also investigated using Hirshfeld surface studies and two-dimensional fingerprint images.

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“…This set of fused rings can be represented by the graph-set notations R 2 2 (8), R 2 4 (8) and R 2 2 (8) (Thanigaimani et al, 2007;Shattock et al, 2008). This type of motif has been reported previously in the crystal structures of trimethoprim hydrogen glutarate (Robert et al, 2001;Ebenezer & Muthiah, 2012) and 2-amino-4-methoxy-6-methylpyridinium trifluoroacetate (Jeevaraj et al, 2016) (Fig. S14 in the supporting information).…”

Section: Molecular Structures and Intermolecular Interactionsmentioning

confidence: 53%

Insights on structure and interactions of 2-amino-4-methoxy-6-methylpyrimidinium salts with 4-aminosalicylate and 5-chlorosalicylate: a combined experimental and theoretical charge–density analysis

Suresh¹,

Kandasamy²,

Balasubramanian³

et al. 2022

Acta Crystallogr C

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The proton-transfer complexes 2-amino-4-methoxy-6-methylpyrimidinium (2A4M6MP) 4-aminosalicylate (4AMSA), C6H10N3O+·C7H6NO3 −, I, and 5-chlorosalicylate (5ClSA), C6H10N3O+·C7H4ClO3 −, II, were synthesized by slow evaporation and crystallized. The crystal structures of both I and II were determined by single-crystal X-ray structure analysis. The crystal structures of both salts exhibit O—H...O, N—H...O, N—H...N and C—H...O interactions in their crystals. The 4AMSA and 5ClSA anions in combination with the 2A4M6MP cations form distinct synthons, which are represented by the graph-set notations R 2 2(8), R 4 2(8) and R 2 2(8). Furthermore, the ΔpK a values were calculated and clearly demonstrate that 2A4M6MP is a good salt former when combined with carboxylic acids. Hirshfeld surface analysis was used to quantify the weak and strong interactions in the solid state, and energy framework calculations showed the stability of the hydrogen-bonding interactions. QTAIM (quantum theory of atoms in molecules) analysis revealed the nature of the chemical bonding in I and II, and the charge–density distribution in the intermolecular interactions in the crystal structures.

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2-Amino-4-methoxy-6-methylpyrimidin-1-ium trifluoroacetate

Cited by 6 publications

References 7 publications

Crystal structure and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 2-hydroxybenzoate

Crystal structure and Hirshfeld surface analysis of 2-amino-4-methoxy-6-methylpyrimidinium 2-hydroxybenzoate

Supramolecular patterns and Hirshfeld surface analysis in the crystal structure of bis(2-amino-4-methoxy-6-methylpyrimidinium) isophthalate

Insights on structure and interactions of 2-amino-4-methoxy-6-methylpyrimidinium salts with 4-aminosalicylate and 5-chlorosalicylate: a combined experimental and theoretical charge–density analysis

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