The Crystal Structures of Some Bromo-Derivatives of the DPPH Stable Free Radical
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. Synthesis
3.2. X-ray Crystallographic Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
References
- Baschieri, A.; Amorati, R. Methods to Determine Chain-Breaking Antioxidant Activity of Nanomaterials beyond DPPH•. A Review. Antioxidants 2021, 10, 1551. [Google Scholar] [CrossRef] [PubMed]
- Prior, R.L.; Wu, X.; Schaich, K. Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements. J. Agric. Food Chem. 2010, 53, 4290–4302. [Google Scholar] [CrossRef] [PubMed]
- Chen, O.; Zhuang, J.; Guzzetta, F.; Lynch, J.; Angerhofer, A.; Cao, Y.C. Synthesis of water-soluble 2,2-diphenyl-1-picrylhydrazyl nanoparticles: A new standard for electron paramagnetic resonance spectroscopy. J. Am. Chem. Soc. 2009, 131, 12542–12543. [Google Scholar] [CrossRef] [PubMed]
- Patrascu, B.; Lete, C.; Popescu, C.; Matache, M.; Paun, A.; Madalan, A.; Ionita, P. Synthesis and spectral comparison of electronic and molecular properties of some hydrazines and hydrazyl free radicals. Arkivoc 2020, vi, 1–10. [Google Scholar] [CrossRef]
- Ionita, P. The Chemistry of DPPH· Free Radical and Congeners. Int. J. Mol. Sci. 2021, 22, 1545. [Google Scholar] [CrossRef] [PubMed]
- Currie, P.F.; Quail, J.W.; Weil, J.A. The reaction between 2,2-diphenyl-1-picrylhydrazyl and bromine. Can. J. Chem. 1980, 58, 723–726. [Google Scholar] [CrossRef]
- Ionita, P. The reaction between DPPH free stable radical and N-bromosuccinimide. South Braz. J. Chem. 1998, 6, 101–106. [Google Scholar] [CrossRef]
- Currie, P.F.; Quail, J.W.; Rusk, A.C.M.; Weil, J.A. A study of Br/NO2 substitution reactions and nuclear magnetic resonance of 2,2-diaryl-1-picrylhydrazines. Can. J. Chem. 1983, 61, 1760–1765. [Google Scholar] [CrossRef]
- Williams, D.E. Crystal structure of 2,2-diphenyl-1-picrylhydrazyl free radical. J. Am. Chem. Soc. 1967, 89, 4280–4287. [Google Scholar] [CrossRef]
- Zilic, D.; Pajic, D.; Juric, M.; Molcanov, K.; Rakvin, B.; Planinic, P.; Zadro, K. Single crystals of DPPH grown from diethyl ether and carbon disulfide solutions- Crystal structures, IR, EPR and magnetization studies. J. Magn. Reson. 2010, 207, 34–41. [Google Scholar] [CrossRef] [PubMed]
- Wang, H.; Barton, R.J.; Robertson, B.E. Crystal and molecular structure of 9-(2,4,6-trinitroanilin)-carbazole. Can. J. Chem. 1987, 65, 1322–1326. [Google Scholar] [CrossRef]
- Gopal, R.; Robertson, B.E.; Weil, J.A. The crystal structure of potassium 1-(N,N-diphenylhydrazono)-2,4,6-trinitrobenzenide. Can. J. Chem. 1983, 61, 2735–2739. [Google Scholar] [CrossRef]
- Wang, H.; Barton, R.J.; Robertson, B.E. Structural studies of 2,2-diphenyl-1-picrylhydrazine: A clathrate forming compound. J. Incl. Phenom. Macrocycl. Chem. 1991, 10, 203–217. [Google Scholar] [CrossRef]
- Kiers, C.T.; de Boer, J.L.; Olthof, R.; Spek, A.L. The crystal structure of a 2,2-diphenyl-1-picrylhydrazyl (DPPH) modification. Acta Crystal. B Struct. Crystal Chem. 1976, 32 B, 2297–2305. [Google Scholar] [CrossRef]
- Ionita, P.; Caproiu, M.T.; Luca, C.; Constantinescu, T.; Caldararu, H.; Balaban, A.T. Selective (15N) nitration of 2,2-diphenyl-1-(2,4- or 2,6-dinitrophenyl)-hydrazines or -hydrazyls. J. Label. Comp. Radiopharm. 1998, 41, 791–799. [Google Scholar] [CrossRef]
Compound | Br-DPPH-H | Br-DPPH | Br2-DPPBr-H DCM |
---|---|---|---|
Chemical formula | C18H12BrN5O6 | C18H11BrN5O6 | C19H13Br3Cl2N4O4 |
M (g mol−1) | 474.24 | 473.23 | 671.96 |
Temperature, (K) | 293(2) | 293(2) | 293(2) |
Wavelength, (Å) | 0.71073 | 0.71073 | 0.71073 |
Crystal system | Orthorhombic | Orthorhombic | Monoclinic |
Space group | P212121 | Pca21 | P21/c |
a (Å) | 9.2057(9) | 13.3163(9) | 8.9757(4) |
b (Å) | 10.9405(10) | 7.3662(4) | 23.8069(11) |
c (Å) | 18.7128(17) | 39.187(2) | 11.0987(5) |
α (°) | 90 | 90 | 90 |
β (°) | 90 | 90 | 94.919(4) |
γ (°) | 90 | 90 | 90 |
V (Å3) | 1884.7(3) | 3843.9(4) | 2362.88(19) |
Z | 4 | 8 | 4 |
Dc (g cm−3) | 1.671 | 1.635 | 1.889 |
F(000) | 592 | 1896 | 1304 |
μ (mm−1) | 2.230 | 2.187 | 5.382 |
Goodness-of-fit for F2 | 1.026 | 1.034 | 1.084 |
Final R1, wR2 [I > 2σ(I)] | 0.0566, 0.1479 | 0.0545, 0.1348 | 0.0601, 0.1541 |
R1, wR2 (all data) | 0.0866, 0.1653 | 0.0800, 0.1505 | 0.0853, 0.1653 |
Largest diff. in peak and hole (eÅ−3) | 0.645, −0.621 | 0.683, −0.315 | 1.206, −0.581 |
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Dobre, A.F.; Madalan, A.M.; Ionita, P. The Crystal Structures of Some Bromo-Derivatives of the DPPH Stable Free Radical. Molbank 2024, 2024, M1880. https://doi.org/10.3390/M1880
Dobre AF, Madalan AM, Ionita P. The Crystal Structures of Some Bromo-Derivatives of the DPPH Stable Free Radical. Molbank. 2024; 2024(3):M1880. https://doi.org/10.3390/M1880
Chicago/Turabian StyleDobre, Adela F., Augustin M. Madalan, and Petre Ionita. 2024. "The Crystal Structures of Some Bromo-Derivatives of the DPPH Stable Free Radical" Molbank 2024, no. 3: M1880. https://doi.org/10.3390/M1880