Four salt phases of theophylline

Buist, Amanda R.; Kennedy, Alan R.; Manzie, Craig

doi:10.1107/s2053229614000825

Cited by 5 publications

(4 citation statements)

References 20 publications

(21 reference statements)

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“…1), obtained from aqueous solution and a methanol hemisolvate, (II) ( Fig. 2), obtained by reacting sulfadiazine with acetyl chloride in methanol [see Buist et al (2014) for another example of the use of these reagents for obtaining differently solvated forms of APIs]. Methanol hemisolvate (II) is isostructural with the ethanol and ethylene glycol solvates described previously by Pan et al (2013).…”

Section: Resultsmentioning

confidence: 97%

Eight salt forms of sulfadiazine

et al. 2014

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Proton transfer to the sulfa drug sulfadiazine [systematic name: 4-amino-N-(pyrimidin-2-yl)benzenesulfonamide] gave eight salt forms. These are the monohydrate and methanol hemisolvate forms of the chloride (2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium chloride monohydrate, C(10)H(11)N(4)O(2)S(+) · Cl(-) · H2O, (I), and 2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium chloride methanol hemisolvate, C(10)H(11)N(4)O(2)S(+) · Cl(-) · (0.5)CH(3)OH, (II)); a bromide monohydrate (2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium bromide monohydrate, C(10)H(11)N(4)O(2)S(+) · Br(-) · H2O, (III)), which has a disordered water channel; a species containing the unusual tetraiodide dianion [bis(2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium) tetraiodide, 2C(10)H(11)N(4)O(2)S(+) · I4(2-), (IV)], where the [I4](2-) ion is located at a crystallographic inversion centre; a tetrafluoroborate monohydrate (2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium tetrafluoroborate monohydrate, C(10)H(11)N(4)O(2)S(+) · BF(4)(-) · H2O, (V)); a nitrate (2-{[(4-azaniumylphenyl)sulfonyl]azanidyl}pyrimidin-1-ium nitrate, C(10)H(11)N(4)O(2)S(+) · NO(3)(-), (VI)); an ethanesulfonate {4-[(pyrimidin-2-yl)sulfamoyl]anilinium ethanesulfonate, C(10)H(11)N(4)O(2)S(+) · C(2)H(5)SO(3)(-), (VII)}; and a dihydrate of the 4-hydroxybenzenesulfonate {4-[(pyrimidin-2-yl)sulfamoyl]anilinium 4-hydroxybenzenesulfonate dihydrate, C(10)H(11)N(4)O(2)S(+) · HOC(6)H(4)SO(3)(-) · 2H2O, (VIII)}. All these structures feature alternate layers of cations and of anions where any solvent is associated with the anion layers. The two sulfonate salts are protonated at the aniline N atom and the amide N atom of sulfadiazine, a tautomeric form of the sulfadiazine cation that has not been crystallographically described before. All the other salt forms are instead protonated at the aniline group and on one N atom of the pyrimidine ring. Whilst all eight species are based upon hydrogen-bonded centrosymetric dimers with graph set R2(2)(8), the two sulfonate structures also differ in that these dimers do not link into one-dimensional chains of cations through NH3-to-SO2 hydrogen-bonding interactions, whilst the other six species do. The chloride methanol hemisolvate and the tetraiodide are isostructural and a packing analysis of the cation positions shows that the chloride monohydrate structure is also closely related to these.

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Section: Resultsmentioning

confidence: 97%

Eight salt forms of sulfadiazine

et al. 2014

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“…The synthesis of the theophylline derivatives has been performed according to the method published by Kennedy et al , 2014. 59 In the case of ThPhyl-BF 4 , it is possible to see the band related to the BF 4 − anion both by FTIR and in the 11 B-NMR spectrum (ESI Fig. S3 to S6 † ).…”

Section: Resultsmentioning

confidence: 99%

Enhancing the stability and efficiency of MAPbI₃ perovskite solar cells by theophylline-BF₄⁻ alkaloid derivatives, a theoretical-experimental approach

González-Juárez

Espinosa-Roa²,

Cadillo-Martínez

et al. 2023

RSC Adv.

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“…The geometric parameters of the title cation are very similar to those known from the literature (Tab. 2) [29].…”

Section: Commentmentioning

confidence: 99%

A cyclic I₁₀ ²⁻ anion in the layered crystal structure of theophyllinium pentaiodide, C₇H₉I₅N₄O₂

Reiß

2019

Zeitschrift Für Kristallographie - New Crystal Structures

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Four salt phases of theophylline

Cited by 5 publications

References 20 publications

Eight salt forms of sulfadiazine

Eight salt forms of sulfadiazine

Enhancing the stability and efficiency of MAPbI₃ perovskite solar cells by theophylline-BF₄⁻ alkaloid derivatives, a theoretical-experimental approach

A cyclic I₁₀ ²⁻ anion in the layered crystal structure of theophyllinium pentaiodide, C₇H₉I₅N₄O₂

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Four salt phases of theophylline

Cited by 5 publications

References 20 publications

Eight salt forms of sulfadiazine

Eight salt forms of sulfadiazine

Enhancing the stability and efficiency of MAPbI3 perovskite solar cells by theophylline-BF4− alkaloid derivatives, a theoretical-experimental approach

A cyclic I10 2− anion in the layered crystal structure of theophyllinium pentaiodide, C7H9I5N4O2

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Enhancing the stability and efficiency of MAPbI₃ perovskite solar cells by theophylline-BF₄⁻ alkaloid derivatives, a theoretical-experimental approach

A cyclic I₁₀ ²⁻ anion in the layered crystal structure of theophyllinium pentaiodide, C₇H₉I₅N₄O₂