5-Nitro-2-furaldehyde semicarbazone

Olszak, T. A.; Peeters, O. M.; Blaton, N. M.; Ranter, C. J. De

doi:10.1107/s0108270194000119

Cited by 7 publications

(9 citation statements)

References 2 publications

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“…The reported melting temperatures are 503-505 K (for the needles) and 511-513 K (for the prisms). Olszak et al (1994) published the first crystal structure of NFZ, which hereafter will be referred to as the -polymorph. The compound crystallized in a monoclinic P2 1 /a space group in the form of a yellow block.…”

Section: Introductionmentioning

confidence: 99%

New polymorphs of an old drug: conformational and synthon polymorphism of 5-nitrofurazone

Pogoda

Janczak

Videnova-Adrabinska

2016

Acta Crystallogr B Struct Sci Cryst Eng Mater

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Two new polymorphic forms of 5-nitrofurazone (5-nitro-2-furaldehyde semicarbazone) have been synthesized and structurally characterized by single-crystal and powder X-ray diffraction methods, vibrational spectroscopy (FT-IR and temperature Raman), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and Hirshfeld surface analysis. The compound crystallizes in three different polymorphic forms P21/a (polymorph α), P21 (polymorph β) and P21/c (polymorph γ), the crystal structures of two of which (polymorphs β and γ) represent new structure determinations. The solid-state molecular organization in the three crystal forms is analyzed and discussed in terms of molecular conformation, crystal packing and hydrogen-bonded networks. All three crystals are formed from trans geometrical isomers, but the molecular conformation of the α-polymorph is syn-anti-anti-anti, while that of β- and γ-polymorphs is syn-anti-syn-syn. As a consequence of this the hydrogen-bond donor and acceptor sites of the molecules are oriented differently, which in turn results in different hydrogen-bond connectivity and packing patterns.

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Section: Introductionmentioning

confidence: 99%

New polymorphs of an old drug: conformational and synthon polymorphism of 5-nitrofurazone

Pogoda

Janczak

Videnova-Adrabinska

2016

Acta Crystallogr B Struct Sci Cryst Eng Mater

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“…The results of the current study suggest that the addition of an equivolume amount or volumetric excess (up to pure solvent) of MeCN gave the polymorphic form 3γ, while the other used pure solvents or solvent mixtures gave the polymorphic form 3β. The known polymorphic form 3α [22] could not be obtained regardless of the crystallization conditions or synthesis method (application of the industrial method, which was the source of form 3α described in [22] also led to form 3β). It can be suggested that form 3β is predominant and form 3α can be a "vanishing polymorph" (in subsequent works [23,24], the presence of form 3α was also not registered).…”

Section: Synthesismentioning

confidence: 99%

“…The bond distances in all studied compounds ( Figure 1) were similar (Table S2). To ensure that the temperature of the measurement did not affect the polymorphic form/stability, the structures of 3β and 3γ were redetermined at 100 K (temperature used in all other measurements of 1-4 structures; in previous studies the 173 K [24] and room temperature [22,23] were used). The compounds 3β and 3γ possessed almost identical structures at all temperatures and slight differences originated from normal changes of atom motion imposed by temperature.…”

Section: Molecular Conformationmentioning

confidence: 99%

“…The presented study demonstrates the complexity of the problem of the self-assembly of different isomorphous molecules (i.e., 5-nitro-2-furaldehyde thiosemicarbazone (1), 5-nitro-2-thiophene thiosemicarbazone (2), 5-nitro-2-furaldehyde semicarbazone (3), 5-nitro-2-thiophene semicarbazone (4), Scheme S1). Only one compound of this group was previously structurally determined (i.e., the 3 [17][18][19]) and it created three monoclinic polymorphic forms 3α [22], 3β, and 3γ [23,24]. The introduction of additional species (different acids) to 3 distinctly affects the present synthons and hydrogen bonding schemes.…”

Section: Introductionmentioning

confidence: 99%

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Interplay between Polymorphism and Isostructurality in the 2-Fur- and 2-Thenaldehyde Semi- and Thiosemicarbazones

Świątkowski

Trzęsowska-Kruszyńska

Danielewicz

et al. 2020

Molecules

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The four compounds, namely: 5-nitro-2-furaldehyde thiosemicarbazone (1); 5-nitro-2-thiophene thiosemicarbazone (2); 5-nitro-2-furaldehyde semicarbazone (3); and 5-nitro-2-thiophene semicarbazone (4) were synthesized and crystallized. The three new crystal structures of 1, 2, and 4 were determined and compared to three already known crystal structures of 3. Additionally, two new polymorphic forms of 1 solvate were synthesized and studied. The influence of the exchange of 2-thiophene to 2-furaldehyde as well as thiosemicarbazone and semicarbazone on the self-assembly of supramolecular nets was elucidated and discussed in terms of the formed synthons and assemblies accompanied by Full Interaction Maps analysis. Changes in the strength of IR oscillators caused by the molecular and crystal packing effects are described and explained in terms of changes of electron density.

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“…S2) and form (CCDC reference 1444951, Fig. S3) (Olszak et al, 1994;Pogoda et al, 2016). After the preparations of the three polymorphs, cooling crystallization experiments in N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO) and N,N-dimethylacetamide (DMAC) with different polymorphs as raw materials were conducted first.…”

Section: Introductionmentioning

confidence: 99%

Molecular conformational evolution mechanism during nucleation of crystals in solution

Wang

Yang

et al. 2020

IUCrJ

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Nucleation of crystals from solution is fundamental to many natural and industrial processes. In this work, the molecular mechanism of conformational polymorphism nucleation and the links between the molecular conformation in solutions and in crystals were investigated in detail by using 5-nitrofurazone as the model compound. Different polymorphs were prepared, and the conformations in solutions obtained by dissolving different polymorphs were analysed and compared. The solutions of 5-nitrofurazone were proven to contain multiple conformers through quantum chemical computation, Raman spectra analysis, 2D nuclear Overhauser effect spectroscopy spectra analysis and molecular dynamics simulation. The conformational evolution and desolvation path was illustrated according to the 1H NMR spectra of solutions with different concentrations. Finally, based on all the above analysis, the molecular conformational evolution path during nucleation of 5-nitrofurazone was illustrated. The results presented in this work shed a new light on the molecular mechanism of conformational polymorphism nucleation in solution.

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5-Nitro-2-furaldehyde semicarbazone

Cited by 7 publications

References 2 publications

New polymorphs of an old drug: conformational and synthon polymorphism of 5-nitrofurazone

New polymorphs of an old drug: conformational and synthon polymorphism of 5-nitrofurazone

Interplay between Polymorphism and Isostructurality in the 2-Fur- and 2-Thenaldehyde Semi- and Thiosemicarbazones

Molecular conformational evolution mechanism during nucleation of crystals in solution

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