Synthesis, Crystal Structure, and Characterization of A New Hydrogen Phosphate Templated By 3-Aminophenyl Sulfone

Mahroug, Adel; Belhouchet, Mohamed; Mhiri, Tahar

doi:10.1080/10426507.2012.690119

Cited by 9 publications

(7 citation statements)

References 14 publications

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“…The overall shape adopted by the 3APS molecule in the hemihydrate species well compares with that observed in the anhydrous crystal forms: in all cases, the two −NH 2 groups are trans disposed with respect to the molecular backbone (Figure 1 right). Interestingly, this conformation is the only one observed in structures, deposited in the CSD, containing neutral 3APS molecules, 15,16,18,20 while in structures containing protonated 3APS molecules, [13][14][15]19,21 only the cis disposition has been found. The angle (α) formed by the mean planes defined by the nonhydrogen atoms of the aromatic moieties in all four investigated 3APS solid forms is comparable to (see Table S2) and in agreement with the structural data deposited in the CSD for the fragment SO 2 (C 6 H 2 R 1 R 2 R 3 ) 2 (only organic, 3D coordinates determined; no ortho substituents, acyclic sulfur).…”

Section: ■ Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 94%

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Molecular-Level Investigation of Hydrate–Anhydrous Phase Transformations of the Dapsone Structurally Related Compound 3,3′-Diaminophenyl Sulfone

Paoli

Lippi

Milazzo

et al. 2022

Crystal Growth & Design

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The solid state of a novel hydrate form of 3,3′diaminophenyl sulfone (3APS_0.5H 2 Oo) as well as its temperatureinduced phase transitions is reported. On increasing the temperature, first a partial dehydration occurs, leading to the partially hydrated 3APS_0.1H 2 Oo, which then transforms into the monoclinic anhydrous form, 3APS_Am. Finally, by recrystallization of the melt 3APS_Am, a second anhydrous orthorhombic phase is obtained (3APS_Ao). This last phase transforms in 3APS_Am at a temperature between 360 and 400 K. XRD, DSC, TGA, HSM, and in silico data have been used to better understand the dehydration mechanism. With the same aim, hydration/ dehydration tests have been carried out. Finally, the dehydration behavior of 3APS_0.5H 2 O has been discussed in comparison with that of the dapsone hydrated phase 4APS_0.33H 2 Om.

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Section: ■ Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 94%

Molecular-Level Investigation of Hydrate–Anhydrous Phase Transformations of the Dapsone Structurally Related Compound 3,3′-Diaminophenyl Sulfone

Paoli

Lippi

Milazzo

et al. 2022

Crystal Growth & Design

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“…599-61-1; molecular structure, Figure ) is an important curing agent of epoxy resins. It is also used as an intermediate of polysulfones, heat-resistant resins, and many other polymers. − Also, 3,3′-diaminodiphenyl sulfone is widely applied to prepare pesticides, medicines, crystal materials, and dyes. , Owing to its low toxicity, 3,3′-diaminodiphenyl sulfone can be employed as a substitute of carcinogenic intermediates, e.g., 3,3′-dimethoxybenzidine . In the industrial process, 3,3′-diaminodiphenyl sulfone is manufactured through reduction of 3,3′-dinitrodiphenyl sulfone.…”

Section: Introductionmentioning

confidence: 99%

“…1−4 Also, 3,3′-diaminodiphenyl sulfone is widely applied to prepare pesticides, medicines, crystal materials, and dyes. 5,6 Owing to its low toxicity, 3,3′-diaminodiphenyl sulfone can be employed as a substitute of carcinogenic intermediates, e.g., 3,3′-dimethoxybenzidine. 6 In the industrial process, 3,3′diaminodiphenyl sulfone is manufactured through reduction of 3,3′-dinitrodiphenyl sulfone.…”

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confidence: 99%

Solubility, Three-Dimensional Hansen Solubility Parameters, and Solution Thermodynamics of 3,3′-Diaminodiphenyl Sulfone in 14 Neat Solvents from 283.15 to 328.15 K

et al. 2021

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By means of the saturation shake-flask technique, the saturation solubility data of 3,3′-diaminodiphenyl sulfone in 14 monosolvents (n-propanol, N,N-dimethylformamide, methanol, ethanol, ethylene glycol, cyclohexane, acetonitrile, isopropanol, water, n-butanol, ethyl acetate, 1,4-dioxane, isobutanol, and 1-heptanol) was achieved at temperatures from 283.15 to 328.15 K and ambient pressure (p = 101.2 kPa). No phenomenon of crystalline form transformation or solvation occurred after dissolution of 3,3′-diaminodiphenyl sulfone in different solvents. The solubility values (mole fraction) of 3,3′-diaminodiphenyl sulfone in above 14 solvents increased as the temperature elevated and obeyed the decreasing tendency in different monosolvents as follows: N,N-dimethylformamide > ethyl acetate > acetonitrile > ethylene glycol > 1,4-dioxane > methanol > ethanol > isobutanol > n-propanol > n-butanol > isopropanol > 1-heptanol > water > cyclohexane. The mutual miscibility of solvent and 3,3′-diaminodiphenyl sulfone was explained through the three-dimensional Hansen solubility parameter. Examination was carried out for molecular interactions between the solute–solvent and solvent–solvent species by means of the linear solvation energy relationships. The solubility data obtained through experiments was correlated by the use of four models/equations, namely, the NRTL model, Apelblat equation, λh equation, and Wilson model. Correlation resulted in the maximum root-mean-square and relative average deviation values of, respectively, 397.1 × 10–5 and 7.57 × 10–2. The Apelblat equation gave lower relative average deviations than the other models/equations for a certain neat solvent. Also, the mixing thermodynamic properties, infinite-dilution activity coefficient, and reduced excess enthalpy were obtained in terms of the Wilson model.

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“…Because the toxicity of 3,3'-diamino diphenyl sulfone is very low, it can substitute carcinogenic intermediates such as 3,3'-dimethoxybenzidine and consequently, it has broad application prospect 5 . Recently, 3,3'-diamino diphenyl sulfone dissolved in ethanol was mixed directly with monophosphoric acid to prepare a new organic-inorganic hybrid crystal material, [C48H51N8O8S4](HPO4)H2PO4, which has a noncentrosymmetric structure and can be a good candidate for nonlinear optic applications 6 . The easiest method of introducing an amino group in 3-position appeared to be by nitration of the proper sulfone, a meta-directing group, followed by reduction 7 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Quality Control of 3,3'-Diamino Diphenyl Sulfone by High Performance Liquid Chromatography

Wei-qun¹,

Lian²,

Jun-qin³

et al. 2014

Asian J. Chem.

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An effective reversed-phase high performance liquid chromatographic method has been developed to separate industrial 3,3'-diamino diphenyl sulfone and its related substances. Separation was achieved on a reversed-phase C18 column with methanol-water (40/60, v/v) as the mobile phase and detection was operated by UV absorption at a wavelength of 250 nm. One unknown impurity, 3,4'-diamino diphenyl sulfone, was identified by the combination of liquid chromatography-mass spectrometry and relationship between RP-HPLC retention and hydrophobicity of the compounds studied. Partial related impurities, 4,4'-diamino diphenyl sulfone, 3,4'-diamino diphenyl sulfone and 3-amino-3'-nitro diphenyl sulfone were determined under the proposed chromatographic condition with relative standard deviations lower than 4.4 %. On the basis of good separation and reliable determination of related substances in 3,3'-diamino diphenyl sulfone, the chromatographic fingerprint of industrial 3,3'-diamino diphenyl sulfone was established, by which quality assessment of 3,3'-diamino diphenyl sulfone could be facilitated for industrial use.

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Synthesis, Crystal Structure, and Characterization of A New Hydrogen Phosphate Templated By 3-Aminophenyl Sulfone

Cited by 9 publications

References 14 publications

Molecular-Level Investigation of Hydrate–Anhydrous Phase Transformations of the Dapsone Structurally Related Compound 3,3′-Diaminophenyl Sulfone

Molecular-Level Investigation of Hydrate–Anhydrous Phase Transformations of the Dapsone Structurally Related Compound 3,3′-Diaminophenyl Sulfone

Solubility, Three-Dimensional Hansen Solubility Parameters, and Solution Thermodynamics of 3,3′-Diaminodiphenyl Sulfone in 14 Neat Solvents from 283.15 to 328.15 K

Synthesis and Quality Control of 3,3'-Diamino Diphenyl Sulfone by High Performance Liquid Chromatography

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