Crystal structure of bis[bis(4-azaniumylphenyl) sulfone] tetranitrate monohydrate

Abstract

In the title compound, the hydrated tetra(nitrate) salt of dapsone (4, 69.69 (19) . In the crystal, mixed cationanion-water molecule layers lying parallel to the (001) plane are formed through N-HÁ Á ÁO, O-HÁ Á ÁO and C-HÁ Á ÁO hydrogen-bonding interactions and these layers are further extended into an overall three-dimensional supramolecular network structure. Inter-ring -interactions are also present [minimum ring centroid separation = 3.693 (3) Å ].

Sulfur Oxidation Increases the Rate of HIRE-Type [1.4]Thiazepinone Ring Expansion and Influences the Conformation of a Medium-Sized Heterocyclic Scaffold

“…We hypothesized that the apparent stabilization of the cis-isomer in 13a could be due to the possible involvement of the sulfone oxygen atoms in intramolecular hydrogen bonding. 12 We studied this phenomenon in detail for 13a (Figure 3). Upon acquiring its EXSY spectrum in DMSO-d 6 , exchange crosspeaks were observed (Figure 3A) suggesting the presence of two isomers in slow exchange.…”

“…For instance, while compound 12a displayed an ∼1:12 cis / trans ratio, for compound 13a the proportion of the cis -isomer was markedly higher and thus the cis / trans ratio was 2:3 (Figure ). We hypothesized that the apparent stabilization of the cis -isomer in 13a could be due to the possible involvement of the sulfone oxygen atoms in intramolecular hydrogen bonding …”

Physico-chemical study of new supramolecular-architectured hybrid organic–inorganic sulfates incorporating diammoniumdiphenylsulfone cations

“… 26 Finally, with an approach closest to ours, in 2017 Benahsese et al synthesized the hydrated tetra-nitrate salt of dapsone. 27 In addition, 3,3′-DDS was reported in the form of a complex with β-cyclodextrin, which resulted in the formation of a twisted intramolecular charge transfer state. 28 Alongside these, the interest in such materials was aroused within our own research group.…”

Investigating the Solubilities of the Nitrate and Isomorphous Bromide and Chloride Salts of Dapsone

“…The first acid constant has a p K a of 2.49 for the equilibrium between ammonium (H 3 N + -aryl) and the neutral form (H 2 N-aryl) and the second has a p K a of 1.30 (monosalt–disalt equilibrium) . It is curious that, besides the potential for salt formation, few salt structures of DDS are known (eight X-ray structures) and only two have pharmaceutical relevance (the mesylate monohydrate and the nitrate hemihydrate). − A search for crystallographic forms of DDS in the Cambridge Structural Database (CSD, v 5.40, November 2018, update 1, Feb 2019) returned five polymorphs, one hydrate (with the unusual DDS: water stoichiometry of 3:1), four solvates with dichloromethane (being two polymorphs), dioxane and tetrahydrofuran, and 12 cocrystals besides the salt structures. − …”