2-Amino-4-methyl-6-oxo-3,6-dihydropyrimidin-1-ium perchlorate–2-amino-6-methylpyrimidin-4(1<i>H</i>)-one–water (1/1/1)

Kaabi, Kamel; Glaoui, Maher El; Ferretti, Valeria; Zeller, Mat­thias; Nasr, C. Ben

doi:10.1107/s1600536811034106

Cited by 9 publications

(4 citation statements)

References 11 publications

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“…Ainsi, chaque atome d'oxygè ne se trouve partagé entre deux sites cristallographiques avec des taux d'occupation de 0,625 (7) et 0,375 (7). Une recherche bibliographique sur les composé s perchloraté s a ré vé lé e l'existence de quatre composé s similaires pré sentant le mê me phé nomè ne de dé sordre (Butcher et al, 2002;Sutha Siluvai et al, 2005;Kaabi et al, 2010Kaabi et al, , 2011 (Bendjeddou et al, 2003;Avecilla et al, 2005;Zhao, 2012;Gholizadeh et al, 2014).…”

Section: Analyse Structuraleunclassified

Structure cristalline et analyses thermique et de surface Hirshfeld du diperchlorate de 4-azaniumyl-2,2,6,6-tétraméthylpipéridin-1-ium

et al. 2017

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The synthesis of 4-azaniumyl-2,2,6,6-tetramethylpiperidin-1-ium diperchlorate, C 9 H 22 N 2 2+ Á2ClO 4 À , was carried out from an aqueous reaction of perchloric acid with 4-amino-2,2,6,6-tetramethylpiperidine. This compound was characterized by TGA-DSC analysis and single-crystal X-ray diffraction. The piperidine ring of the dication adopts a chair conformation and the orientation of the C-NH 3 bond is equatorial. One of the two crystallographically independent perchlorate anions exhibits disorder [occupancies 0.625 (7) and 0.375 (7)]. The crystal packing is constituted by a succession of mixed layers parallel to the (102) plane, made up of C 9 H 22 N 2 2+ dications and ClO 4 À anions. These ions are linked by normal and bifurcated N-HÁ Á ÁO hydrogen bonds with R 4 4 (12) graph-set motifs, generating a two-dimensional network. The intermolecular interactions in the crystal structure were quantified and analysed using Hirshfeld surface analysis. Contexte chimiqueLes maté riaux hybrides 'organique-inorganique' sont l'objet d'un inté rê t sans cesse croissant permettant d'allier à la fois certaines proprié té s d'un maté riau inorganique (ou d'une molé cule inorganique), et certaines proprié té s d'un polymè re (ou d'une molé cule organique). Cette symbiose entre deux mondes de la chimie trop longtemps considé ré s comme antagonistes peut aussi amener à des proprié té s complè tement nouvelles, et ouvre un vaste champ d'investigations pour le chimiste.

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Section: Analyse Structuraleunclassified

Structure cristalline et analyses thermique et de surface Hirshfeld du diperchlorate de 4-azaniumyl-2,2,6,6-tétraméthylpipéridin-1-ium

et al. 2017

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“…On this basis, three CSD searches for CIC, BMIC and 6-methylisocytosine (MIC), which were restricted to organic compounds with determined three-dimensional coordinates and including either the 1H-or 3H-tautomeric form, were performed and yielded only 12 unique structures of MIC. These results can be divided into three salts [CSD refcode XOWKOK (Oueslati et al, 2009), YOCZUN (Wang et al, 2014) and EXIPOR (Kaabi et al, 2011)], two entries that contain solely the 1H-tautomer [FETSEC (Lowe et al, 1987) A perspective view of (III), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and hydrogen bonds are displayed as dashed lines.…”

Section: Figurementioning

confidence: 99%

6-Chloroisocytosine and 5-bromo-6-methylisocytosine: again, one or two tautomers present in the same crystal?

Gerhardt

Bolte

2016

Acta Crystallogr C

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It is well known that pyrimidin-4-one derivatives are able to adopt either the 1H- or the 3H-tautomeric form in (co)crystals, depending on the coformer. As part of ongoing research to investigate the preferred hydrogen-bonding patterns of active pharmaceutical ingredients and their model systems, 2-amino-6-chloropyrimidin-4-one and 2-amino-5-bromo-6-methylpyrimidin-4-one have been cocrystallized with several coformers and with each other. Since Cl and Br atoms both have versatile possibilities to interact with the coformers, such as via hydrogen or halogen bonds, their behaviour within the crystal packing was also of interest. The experiments yielded five crystal structures, namely 2-aminopyridin-1-ium 2-amino-6-chloro-4-oxo-4H-pyrimidin-3-ide-2-amino-6-chloropyrimidin-4(3H)-one (1/3), C5H7N2(+)·C4H3ClN3O(-)·3C4H4ClN3O, (Ia), 2-aminopyridin-1-ium 2-amino-6-chloro-4-oxo-4H-pyrimidin-3-ide-2-amino-6-chloropyrimidin-4(3H)-one-2-aminopyridine (2/10/1), 2C5H7N2(+)·2C4H3ClN3O(-)·10C4H4ClN3O·C5H6N2, (Ib), the solvent-free cocrystal 2-amino-5-bromo-6-methylpyrimidin-4(3H)-one-2-amino-5-bromo-6-methylpyrimidin-4(1H)-one (1/1), C5H6BrN3O·C5H6BrN3O, (II), the solvate 2-amino-5-bromo-6-methylpyrimidin-4(3H)-one-2-amino-5-bromo-6-methylpyrimidin-4(1H)-one-N-methylpyrrolidin-2-one (1/1/1), C5H6BrN3O·C5H6BrN3O·C5H9NO, (III), and the partial cocrystal 2-amino-5-bromo-6-methylpyrimidin-4(3H)-one-2-amino-5-bromo-6-methylpyrimidin-4(1H)-one-2-amino-6-chloropyrimidin-4(3H)-one (0.635/1/0.365), C5H6BrN3O·C5H6BrN3O·C4H4ClN3O, (IV). All five structures show R2(2)(8) hydrogen-bond-based patterns, either by synthon 2 or by synthon 3, which are related to the Watson-Crick base pairs.

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“…In fact, the widespread occurrence of perchlorates has generated considerable interest in diverse elds, particularly, stabilization of PVC, catalysis and pharmacology [11][12][13]. As a result, perchlorates have been often employed as inorganic building blocks in hybrid compounds with multi-dimensional shapes likely chains, ribbons, layers, or three-dimensional arrangements [14][15][16]. Bene ting from structural diversities and characteristics of hybrid materials, organic components are an appealing part of hybrid materials, which play important roles in affecting their physical properties.…”

Section: Introductionmentioning

confidence: 99%

Antispasmodic activity of novel 2,4-dichloroanilinium perchlorate hybrid material (I): X-ray crystallography, DFT studies, and molecular docking approach

Jaziri¹,

Louis

Gharbi³

et al. 2022

Preprint

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The intriguing properties of organic-inorganic hybrid materials has resulted in the recent upsurge for more effective hybrid materials with diverse activity, harnessing the advantage of the flexibility and structural diversity imposed by these materials. In line with these, the synthesis, crystallography and structural characterization of a novel perchlorate (2,4-dichloroanilinium perchlorate) organic-inorganic hybrid material is reported. The synthesized structure was characterized by FTIR and NMR techniques. Appropriate computational methods were utilized to correlate the experimentally observed spectroscopic properties as well as other molecular electronic properties. The computational studies were achieved at the DFT/M06-2X/6-311++G(2df,2dp) and aug-cc-pVTZ level of theory. For benchmarking purposes, the PWPB95 functional with D3BJ dispersion correction was utilized. Molecular electronic properties such as the frontier molecular orbitals, Natural bond orbital analysis, Hirshfeld surface analysis, and visual study of weak interaction via non-covalent interaction were considered to understand the molecular diversity of the perchlorate cluster. Hybrid materials often pose diverse bio-activities and as such the anti-spasmodic activity of the studied compound is considered by molecular docking approach.

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2-Amino-4-methyl-6-oxo-3,6-dihydropyrimidin-1-ium perchlorate–2-amino-6-methylpyrimidin-4(1H)-one–water (1/1/1)

Cited by 9 publications

References 11 publications

Structure cristalline et analyses thermique et de surface Hirshfeld du diperchlorate de 4-azaniumyl-2,2,6,6-tétraméthylpipéridin-1-ium

Structure cristalline et analyses thermique et de surface Hirshfeld du diperchlorate de 4-azaniumyl-2,2,6,6-tétraméthylpipéridin-1-ium

6-Chloroisocytosine and 5-bromo-6-methylisocytosine: again, one or two tautomers present in the same crystal?

Antispasmodic activity of novel 2,4-dichloroanilinium perchlorate hybrid material (I): X-ray crystallography, DFT studies, and molecular docking approach

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