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Journal articles on the topic 'Nitroxide radicals'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Bognár, Balázs, Györgyi Úr, Cecília Sár, Olga H. Hankovszky, Kálmán Hideg, and Tamás Kálai. "Synthesis and Application of Stable Nitroxide Free Radicals Fused with Carbocycles and Heterocycles." Current Organic Chemistry 23, no. 4 (2019): 480–501. http://dx.doi.org/10.2174/1385272823666190318163321.

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Stable nitroxide free radicals have traditionally been associated with 2,2,6,6- tetramethylpiperidine-1-oxyl (TEMPO) or its 4-substituted derivatives as relatively inexpensive and readily accessible compounds with limited possibilities for further chemical modification. Over the past two decades, there has been a resurgence of interest in stable free radicals with proper functionalization tuned for various applications. The objective of this review is to present recent results with synthetic methodologies to achieve stable nitroxide free radicals fused with aromatic carbocycles and heterocycle

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2

Romanov, Vasily, Irina Bagryanskaya, Dmitry Gorbunov, et al. "A Crystallographic Study of a Novel Tetrazolyl-Substituted Nitronyl Nitroxide Radical." Crystals 8, no. 9 (2018): 334. http://dx.doi.org/10.3390/cryst8090334.

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Spin-labelled compounds are widely used in chemistry, physics, biology, and material sciences, but the directed synthesis of some functionalized organic radicals is still a challenge. We succeeded in the preparation of a tetrazolyl-substituted nitronyl nitroxide radical in pure crystalline form. According to the single-crystal X-ray data, intra- (NH…O, 2.43 Å) and inter-molecular hydrogen bonds (NH…O, 1.91 Å) are formed between NH groups of the tetrazole cycles and O atoms of the paramagnetic moieties. The intermolecular H-bonds connect the molecules forming chains along the a-axis. Moreover,

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3

Hussain, Hamza A. "The effect of cation concentration on the nitrogen splitting constant of nitroxide free radicals." Collection of Czechoslovak Chemical Communications 55, no. 10 (1990): 2377–80. http://dx.doi.org/10.1135/cccc19902377.

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Nitroxide free radicals prepared from diethylamine, piperidine and pyrrolidine by oxidation with hydrogen peroxide were studied by ESR spectroscopy. The changes in the 14N splitting constant (aN) caused by the addition of KBr or tetraethylammonium bromide were measured in dependence on the concentration of the ions. For diethylamine nitroxide and piperidine nitroxide, the results are discussed in terms of two equilibria: the one, involving the anion, is associated with a gain or loss of hydrogen bonds to the nitroxide oxygen atom, the other is associated with the formation of solvent shared un

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4

Kokorin, Alexander I., and Igor A. Grigor’ev. "Fluorinated nitroxide radicals." Mendeleev Communications 16, no. 4 (2006): 195–200. http://dx.doi.org/10.1070/mc2006v016n04abeh002329.

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5

Constantinescu, Titus, Petre Ionita, Ion Chiorescu, and Gabriela Ionita. "Hydrazyl, Nitronyl-, and imino-nitroxides: Synthesis, properties and reaction with nitric oxide and nitrogen dioxide." Open Chemistry 1, no. 4 (2003): 465–76. http://dx.doi.org/10.2478/bf02475228.

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AbstractTen novel and stable free radicals of nitronyl-, imino-nitroxide and hydrazyl type compounds were synthesized and their physico-chemical properties investigated. UV-Vis and ESR spectroscopic data, as well as the lipophilicities and specific hydrophobic areas of the compounds are compiled. The reaction of these radical compounds with nitric oxide and nitrogen dioxide was also investigated. The radicals synthesized, show selectivity in their reaction with these nitric oxides, depending on their structure (nitronyl-nitroxide radicals react with NO, while hydrazyl radicals react with NO2).

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6

Kulis, Jakov, Craig A. Bell, Aaron S. Micallef, and Michael J. Monteiro. "Ultrafast and Reversible Multiblock Formation by the SET-Nitroxide Radical Coupling Reaction." Australian Journal of Chemistry 63, no. 8 (2010): 1227. http://dx.doi.org/10.1071/ch10092.

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The single electron transfer-nitroxide radical coupling (SET-NRC) reaction has been used to produce multiblock polymers with high molecular weights in under 3 min at 50°C by coupling a difunctional telechelic polystyrene (Br-PSTY-Br) with a dinitroxide. The well known combination of dimethyl sulfoxide as solvent and Me6TREN as ligand facilitated the in situ disproportionation of CuIBr to the highly active nascent Cu0 species. This SET reaction allowed polymeric radicals to be rapidly formed from their corresponding halide end-groups. Trapping of these carbon-centred radicals at close to diffus

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7

Politanskaya, Larisa V., Pavel A. Fedyushin, Tatyana V. Rybalova, Artem S. Bogomyakov, Nargiz B. Asanbaeva, and Evgeny V. Tretyakov. "Fluorinated Organic Paramagnetic Building Blocks for Cross-Coupling Reactions." Molecules 25, no. 22 (2020): 5427. http://dx.doi.org/10.3390/molecules25225427.

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New stable polyfluorinated nitroxide radicals for use in cross-coupling reactions, namely, N-tert-butyl-N-oxyamino-2,3,5,6-tetrafluoro-4-iodobenzene and N-tert-butyl-N-oxyamino-2,3,5,6-tetrafluoro-4-ethynylbenzene, were prepared from perfluoroiodobenzene. The reaction of the polyfluoro derivative with tert-butylamine under autoclaving conditions leading to the formation of N-tert-butyl-2,3,5,6-tetrafluoro-4-iodoaniline proved to be the key stage of the whole process. The fluorinated tert-butyl iodophenyl nitroxide was found to form in a solid state via N–O···I halogen bonds, a one-dimensional

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8

Bekö, Sándor L., Silke D. Thoms, and Martin U. Schmidt. "4,4′-{Diazenediylbis[(1,4-phenylene)bis(carbonyloxy)]}bis(2,2,6,6-tetramethylpiperidinyloxidanyl): the first crystal structure determination from powder data of a nitroxide radical." Acta Crystallographica Section C Crystal Structure Communications 69, no. 12 (2013): 1513–15. http://dx.doi.org/10.1107/s0108270113029211.

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The title compound, C32H42N4O6, is a novel nitroxide radical used for pulsed electron-electron double resonance (PELDOR) spectroscopy. Its crystal structure was determined from laboratory X-ray powder diffraction data. The attractive forces between the molecules in the crystal structure are mainly of dispersive nature. A special interaction of the nitroxide radicals was not observed.

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9

Al-Bala'a, Imad, and Richard D. Bates. "Effects of Multiple Binding Sites on Studies of Hydrogen Bonding between Nitroxide Radicals and Solvent Molecules." Collection of Czechoslovak Chemical Communications 58, no. 1 (1993): 47–52. http://dx.doi.org/10.1135/cccc19930047.

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The role of more than one binding site on a nitroxide free radical in magnetic resonance determinations of the properties of the complex formed with a hydrogen donor is examined. The expression that relates observed hyperfine couplings in EPR spectra to complex formation constants and concentrations of each species in solution becomes much more complex when multiple binding sites are present, but reduces to a simpler form when binding at the two sites occurs independently and the binding at the non-nitroxide site does not produce significant differences in the hyperfine coupling constant in th

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10

Lu, Jiao, Pei Jing, Chaoyi Jin, Junfang Xie, and Licun Li. "Modulating the magnetization dynamics in Ln–Cu-Rad hetero-tri-spin complexes through cis/trans coordination of nitronyl nitroxide radicals around the metal center." Dalton Transactions 50, no. 9 (2021): 3280–88. http://dx.doi.org/10.1039/d1dt00090j.

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11

Golly, I., and P. Hlavica. "N-Oxidation of 4-chloroaniline by prostaglandin synthase. Redox cycling of radical intermediate(s)." Biochemical Journal 226, no. 3 (1985): 803–9. http://dx.doi.org/10.1042/bj2260803.

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4-Chloroaniline undergoes N-oxidation in ram seminal-vesicle microsomal preparations supplemented with arachidonic acid to yield N-(4-chlorophenyl)-hydroxylamine and 1-chloro-4-nitrosobenzene. H2O2 also supports metabolism of the amine substrate to the same organic-solvent-extractable products, suggesting that the hydroperoxidase activity of prostaglandin synthase is responsible for the co-oxidation. Analysis of the reaction mixtures by e.s.r. spectrometry reveals the formation of a radical intermediate bearing the characteristics of a strongly immobilized nitroxide. Arylamine-stimulated O2.-

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12

Griesar, K., E. A. Soto-Bustamante, and W. Haase. "Darstellung und magnetische Eigenschaften einiger kristalliner Nitroxidradikale/Synthesis and Magnetic Properties of Some Crystalline Nitroxide Radicals." Zeitschrift für Naturforschung B 55, no. 7 (2000): 567–75. http://dx.doi.org/10.1515/znb-2000-0703.

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Abstract The syntheses of different nitroxide radicals are reported. The thermal behaviour of the ni troxide radicals was examined by polarizing microscopy, differential scanning calorimetry as well as X-ray diffraction experiments. Temperature dependent magnetic susceptibility measurements were carried out in order to determine the magnetic properties of these nitroxide radicals. The majority of the radicals presented here show weak antiferromagnetic exchange interactions.

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13

Lee, Hamilton, Arezoo Shahrivarkevishahi, Jenica L. Lumata, et al. "Supramolecular and biomacromolecular enhancement of metal-free magnetic resonance imaging contrast agents." Chemical Science 11, no. 8 (2020): 2045–50. http://dx.doi.org/10.1039/c9sc05510j.

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Supramolecular/macromolecular organic radical contrast agents (smORCAs) overcome many of the limitations of nitroxide radicals for use in magnetic resonance imaging in vivo like poor stability and weak contrast.

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14

Awaga, Kunio, Tamotsu Inabe, Umpei Nagashima та ін. "α-Nitronyl Nitroxide Cation Radicals". Chemistry Letters 20, № 10 (1991): 1777–80. http://dx.doi.org/10.1246/cl.1991.1777.

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15

Krzyczmonik, Paweł, and Henryk Scholl. "Electrode reactions of nitroxide radicals." Journal of Electroanalytical Chemistry 335, no. 1-2 (1992): 233–51. http://dx.doi.org/10.1016/0022-0728(92)80245-y.

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16

Sies, Helmut, and Rolf Mehlhorn. "Mutagenicity of nitroxide-free radicals." Archives of Biochemistry and Biophysics 251, no. 1 (1986): 393–96. http://dx.doi.org/10.1016/0003-9861(86)90087-1.

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17

Wang, Jiahu, and Vedene H. Smith, Jr. "Ab initio Study of the Spin Density of Nitroxide Radicals." Zeitschrift für Naturforschung A 48, no. 1-2 (1993): 109–16. http://dx.doi.org/10.1515/zna-1993-1-225.

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Abstract The spin densities of the nitroxides H2NO, (CH3)HNO and (CH3)2 NO have been studied by iterative CI methods. Calculations at different geometries with various basis sets were performed. It is found that the spin distribution is delocalized within the N-O group, and substitution of the hydrogen atoms on the nitroxyl group by methyl groups changes the spin distribution significantly. Electron correlation, as well as the basis-set quality, plays an important role for the fluctuation of spin populations in the nitroxide radicals. It has been found that the spin density map can be predicte

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18

Önal, Emel, Yusuf Yerli, Bunyemin Cosut, et al. "Nitronyl and imino nitroxide free radicals as precursors of magnetic phthalocyanine and porphyrin building blocks." New J. Chem. 38, no. 9 (2014): 4440–47. http://dx.doi.org/10.1039/c4nj00574k.

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19

Lemaire, M. T. "Recent developments in the coordination chemistry of stable free radicals." Pure and Applied Chemistry 76, no. 2 (2004): 277–93. http://dx.doi.org/10.1351/pac200476020277.

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Several advances in the coordination chemistry of stable free-radical species over the past six years are documented in this review article. Specifically, a number of recent reports focused on the coordination chemistry of chelating nitroxide ligands are highlighted, with an emphasis on enhanced magnetic or optical properties in these complexes. Furthermore, very intriguing recent magnetic and optical studies with one-dimensional nitroxide chain complexes (new "Glauber" chains and chiral magnets) are also discussed. The verdazyls are another family of stable radicals whose coordination chemist

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20

Gotoh, Hiroaki, Jun Naganuma, Shinya Nitta, and Yudai Yamazaki. "Structural and electronic factors relating to the stability of imidazolidine nitroxide radicals." SDRP Journal of Computational Chemistry & Molecular Modelling 4, no. 1 (2020): 321–27. http://dx.doi.org/10.25177/jccmm.4.1.ra.10600.

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21

Romanov, Vasily, Irina Bagryanskaya, Nina Gritsan, et al. "Assembly of Imidazolyl-Substituted Nitronyl Nitroxides into Ferromagnetically Coupled Chains." Crystals 9, no. 4 (2019): 219. http://dx.doi.org/10.3390/cryst9040219.

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New nitronyl nitroxides, namely, 2-(4,5-dimethylimidazol-2-yl)- and 2-(4,5-dichloroimidazol-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl, were prepared in crystalline form. According to single-crystal X-ray data, intra- and intermolecular hydrogen bonds are formed between NH groups of the imidazole cycles and O atoms of the nitroxide moieties. The intermolecular H-bonds contribute to the alignment of molecules into chains along the a-axis; this alignment causes short intrachain contacts between O and C atoms carrying spin density of opposite signs. Such an arrangement of ni

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22

Suzuki, Shuichi, Sayaka Kira, Masatoshi Kozaki, et al. "An efficient synthetic method for organometallic radicals: structures and properties of gold(i)-(nitronyl nitroxide)-2-ide complexes." Dalton Transactions 46, no. 8 (2017): 2653–59. http://dx.doi.org/10.1039/c6dt04685a.

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One-pot synthesis of (nitronyl nitroxide)-gold(i)-phosphine (NN-Au-P) complexes has been developed using chloro(tetrahydrothiophene)gold(i), phosphine ligands, nitronyl nitroxide radicals, and sodium hydroxide.

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23

Buta, Maria Cristina, Ana Maria Toader, Bogdan Frecus, Corneliu I. Oprea, Fanica Cimpoesu, and Gabriela Ionita. "Molecular and Supramolecular Interactions in Systems with Nitroxide-Based Radicals." International Journal of Molecular Sciences 20, no. 19 (2019): 4733. http://dx.doi.org/10.3390/ijms20194733.

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Nitroxide-based radicals, having the advantage of firm chemical stability, are usable as probes in the detection of nanoscale details in the chemical environment of various multi-component systems, based on subtle variations in their electron paramagnetic resonance spectra. We propose a systematic walk through the vast area of problems and inquires that are implied by the rationalization of solvent effects on the spectral parameters, by first-principle methods of structural chemistry. Our approach consists of using state-of-the-art procedures, like Density Functional Theory (DFT), on properly

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24

Queiroz, Raphael F., Verônica Paviani, Fernando R. Coelho, Emerson F. Marques, Paolo Di Mascio, and Ohara Augusto. "The carbonylation and covalent dimerization of human superoxide dismutase 1 caused by its bicarbonate-dependent peroxidase activity is inhibited by the radical scavenger tempol." Biochemical Journal 455, no. 1 (2013): 37–46. http://dx.doi.org/10.1042/bj20130180.

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The nitroxide tempol inhibited the carbonylation and covalent dimerization of human superoxide dismutase 1 caused by its bicarbonate-dependent peroxidase activity. Tempol acted by scavenging the produced carbonate radical and by recombining with hSOD1-Trp32• radicals as indicated by MS/MS evidence.

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25

Li, Hongdao, Jiao Lu, Jing Xie, Pei Jing, and Licun Li. "Two-Dimensional Nitronyl Nitroxide–Cu Networks Based on Multi-Dentate Nitronyl Nitroxides: Structures and Magnetic Properties." Magnetochemistry 7, no. 5 (2021): 73. http://dx.doi.org/10.3390/magnetochemistry7050073.

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Two multi-dentate nitronyl nitroxide radicals, namely, bisNITPhPy ([5-(4-pyridyl)-1,3-bis(1′-oxyl-3′-oxido-4′,4′,5′,5′-tetramethyl-4,5-hydro-1H-imidazol-2-yl)]benzene) and NIT-3Py-5-4Py (2-{3-[5-(4-pyridyl)]pyridyl}-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide), were assembled with CuII ions to obtain two-dimensional heterospin 2p–3d coordination polymers [Cu7(hfac)14(bisNITPhPy)2]n (1) and [Cu2(hfac)4(NIT-3Py-5-4Py)]n (2) (hfac: hexafluoroacetylacetonate). In both compounds, the bisNITPhPy and NIT-3Py-5-3Py radicals acted as pentadentate and tetradentate ligands, respectively, to connect wit

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26

Rizzardo, Ezio, and David H. Solomon. "On the Origins of Nitroxide Mediated Polymerization (NMP) and Reversible Addition–Fragmentation Chain Transfer (RAFT)." Australian Journal of Chemistry 65, no. 8 (2012): 945. http://dx.doi.org/10.1071/ch12194.

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The early experiments on radical polymerization, which were to lead to a study of nitroxide trapping of the initiation step and the interest in defect groups, particularly the macromonomers formed by termination by disproportionation, are discussed. Results from the nitroxide trapping clearly show that the initiation step ranges from simple clean addition to the head of the monomer, to complex addition/abstraction reactions. Careful selection of the monomer/initiation system is emphasized with particular reference to two common monomers, styrene and methyl methacrylate, and two initiating radi

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27

Brustolon, M., A. L. Maniero, M. F. Ottaviani, M. Romanelli, and U. Segre. "Proton hyperfine tensors in nitroxide radicals." Journal of Physical Chemistry 94, no. 17 (1990): 6589–94. http://dx.doi.org/10.1021/j100380a013.

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28

Li, Fei, Yanpu Zhang, Se Ra Kwon, and Jodie L. Lutkenhaus. "Electropolymerized Polythiophenes Bearing Pendant Nitroxide Radicals." ACS Macro Letters 5, no. 3 (2016): 337–41. http://dx.doi.org/10.1021/acsmacrolett.5b00937.

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29

Minguet, Maria, David B. Amabilino, Joan Cirujeda та ін. "Stereochemistry of Phenylα-Nitronyl Nitroxide Radicals". Chemistry - A European Journal 6, № 13 (2000): 2350–61. http://dx.doi.org/10.1002/1521-3765(20000703)6:13<2350::aid-chem2350>3.0.co;2-u.

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30

Mannini, Matteo, Donella Rovai, Lorenzo Sorace, et al. "Patterned monolayers of nitronyl nitroxide radicals." Inorganica Chimica Acta 361, no. 12-13 (2008): 3525–28. http://dx.doi.org/10.1016/j.ica.2008.03.008.

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31

Elajaili, Hanan, Jessica Sedhom, Sandra S. Eaton, and Gareth R. Eaton. "Persistence of Nitroxide Radicals in Solution." Applied Magnetic Resonance 50, no. 10 (2019): 1177–81. http://dx.doi.org/10.1007/s00723-019-01135-7.

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32

Fettouhi, Mohammed. "Benzo-15-Crown-5 Based Nitronyl-Nitroxide and Imino-Nitroxide Radicals." Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals 356, no. 1 (2001): 365–69. http://dx.doi.org/10.1080/10587250108023715.

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33

Sugano, Tadashi, Stephen J. Blundell, Francis L. Pratt, et al. "Magnetism in Nitronyl Nitroxide Radicals and their Ion Radical Salts." Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals 305, no. 1 (1997): 435–44. http://dx.doi.org/10.1080/10587259708045078.

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34

Nagasaki, Yukio. "Nitroxide radicals and nanoparticles: a partnership for nanomedicine radical delivery." Therapeutic Delivery 3, no. 2 (2012): 165–79. http://dx.doi.org/10.4155/tde.11.153.

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35

Han, Wen-Juan, Lei Chen, Hai-Bo Wang, et al. "A Novel Nitronyl Nitroxide with Salicylic Acid Framework Attenuates Pain Hypersensitivity and Ectopic Neuronal Discharges in Radicular Low Back Pain." Neural Plasticity 2015 (2015): 1–14. http://dx.doi.org/10.1155/2015/752782.

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Evidence has accumulated that reactive oxygen species and inflammation play crucial roles in the development of chronic pain, including radicular low back pain. Nonsteroid anti-inflammatory drugs (NSAIDs), for example, salicylic acid, aspirin, provided analgesic effects in various types of pain. However, long-term use of these drugs causes unwanted side effects, which limits their implication. Stable nitronyl (NIT) nitroxide radicals have been extensively studied as a unique and interesting class of new antioxidants for protection against oxidative damage. The present study synthesized a novel

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36

Aliaga, C., S. Michea, C. Pastenes, J. Salazar, and M. C. Rezende. "On the interactions of TEMPO radicals with gold nanostructures." New Journal of Chemistry 42, no. 12 (2018): 9764–70. http://dx.doi.org/10.1039/c7nj04714b.

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37

Yan, Guo-Ping, Kathryn E. Fairfull-Smith, Craig D. Smith, Graeme R. Hanson, and Steven E. Bottle. "Porphyrin containing isoindoline nitroxides as potential fluorescence sensors of free radicals." Journal of Porphyrins and Phthalocyanines 15, no. 04 (2011): 230–39. http://dx.doi.org/10.1142/s1088424611003203.

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A series of new spin-labeled porphyrin containing isoindoline nitroxide moieties were synthesized and characterized as potential free radical fluorescence sensors. Fluorescence-suppression was observed in the free-base monoradical porphyrins, whilst the free-base biradical porphyrins exhibited highly suppressed fluorescence about three times greater than the monoradical porphyrins. The observed fluorescence-suppression was attributed to enhanced intersystem crossing resulting from electronexchange between the doublet nitroxide and the excited porphyrin fluorophore. Notably, fluorescencesuppres

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38

Ishii, Kazuyuki, Shoji Takeuchi, Shinsuke Shimizu та Nagao Kobayashi. "A Concept for Controlling Singlet Oxygen (1Δg) Yields Using Nitroxide Radicals: Phthalocyaninatosilicon Covalently Linked to Nitroxide Radicals". Journal of the American Chemical Society 126, № 7 (2004): 2082–88. http://dx.doi.org/10.1021/ja035352v.

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Żamojć, Krzysztof, Irena Bylińska, Wiesław Wiczk, and Lech Chmurzyński. "Fluorescence Quenching Studies on the Interactions between Chosen Fluoroquinolones and Selected Stable TEMPO and PROXYL Nitroxides." International Journal of Molecular Sciences 22, no. 2 (2021): 885. http://dx.doi.org/10.3390/ijms22020885.

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The influence of the stable 2,2,6,6-tetramethylpiperidinyl-N-oxyl (TEMPO) nitroxide and its six C4-substituted derivatives, as well as two C3-substituted analogues of 2,2,5,5-tetramethylpyrrolidynyl-N-oxyl (PROXYL) nitroxide on the chosen fluoroquinolone antibiotics (marbofloxacin, ciprofloxacin, danofloxacin, norfloxacin, enrofloxacin, levofloxacin and ofloxacin), has been examined in aqueous solutions by UV absorption as well as steady-state and time-resolved fluorescence spectroscopies. The mechanism of fluorescence quenching has been specified and proved to be purely dynamic (collisional)

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40

Smith, Peter, and Jill Suzanne Robertson. "Electron paramagnetic resonance study of the reactions of the spin trap 3,5-dibromo-4-nitrosobenzenesulfonate." Canadian Journal of Chemistry 66, no. 5 (1988): 1153–58. http://dx.doi.org/10.1139/v88-189.

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Using rapid-mixing, continuous-flow TiCl3-based techniques and also by means of static-sample studies involving the thermal decomposition of symmetric aliphatic azo compounds, we have characterized by electron paramagnetic resonance 22 spin adducts of 3,5-dibromo-4-nitrosobenzenesulphonate, 1, in aqueous solution at 25 °C. These spin adducts, all nitroxides, exhibit a moderately wide range of a-nitrogen and β-CH proton splitting constants, which we discuss in terms of steric and electronic effects. In connection with these studies, blank experiments showed that aqueous solutions of 1 gave no r

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41

Busfield, WK, DI Grice, ID Jenkins, and SH Thang. "Reaction of t-Butoxy Radicals With Cyclic Alkenes Studied by the Nitroxide Radical-Trapping Technique." Australian Journal of Chemistry 44, no. 10 (1991): 1407. http://dx.doi.org/10.1071/ch9911407.

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The pattern of reactions occurring between t- butoxy radicals and a number of cyclic alkenes has been investigated by the nitroxide radical-trapping technique. The major reaction pathway is allylic abstraction unless this position is at a bridgehead as in norbornene where the major pathway is radical addition. The technique is sufficiently sensitive to identify minor reaction pathways of non-allylic substitution and radical addition when in the presence of extensive allylic substitution. Some stereoselective effects are also detected.

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42

Smith, Craig D., John P. Bartley, and Steven E. Bottle. "Electrospray mass spectrometry of stable iminyl nitroxide and nitronyl nitroxide free radicals." Journal of Mass Spectrometry 37, no. 9 (2002): 897–902. http://dx.doi.org/10.1002/jms.339.

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43

Busfield, W. Ken, W. Ken Busfield, Ian D. Jenkins, Ian D. Jenkins, Michael J. Monteiro, and Michael J. Monteiro. "Initiation Processes in Copolymerization Studied by the Nitroxide Radical-Trapping Technique: Ethyl Vinyl Ether and Acrylonitrile." Australian Journal of Chemistry 50, no. 1 (1997): 1. http://dx.doi.org/10.1071/c96016.

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The nitroxide free-radical trapping technique has been applied to an investigation of the initiation mechanism of the copolymerization of ethyl vinyl ether and acrylonitrile initiated by t-butoxyl radicals. In addition to a range of products normally produced from reactions with individual monomers, four new trapped products each involving both monomers have been observed. These arise because the strongly electron-accepting acrylonitrile reacts so fast with the strongly nucleophilic ethyl vinyl ether radical end groups that the reaction competes successfully with radical trapping. t-Butoxyl ra

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Yu, Hui, Linying Cao, Feifei Li, et al. "The antioxidant mechanism of nitroxide TEMPO: scavenging with glutathionyl radicals." RSC Advances 5, no. 78 (2015): 63655–61. http://dx.doi.org/10.1039/c5ra06129f.

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Zaytseva, Elena, and Dmitrii Mazhukin. "Spirocyclic Nitroxides as Versatile Tools in Modern Natural Sciences: From Synthesis to Applications. Part I. Old and New Synthetic Approaches to Spirocyclic Nitroxyl Radicals." Molecules 26, no. 3 (2021): 677. http://dx.doi.org/10.3390/molecules26030677.

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Abstract:

Spirocyclic nitroxyl radicals (SNRs) are stable paramagnetics bearing spiro-junction at α-, β-, or γ-carbon atom of the nitroxide fragment, which is part of the heterocyclic system. Despite the fact that the first representatives of SNRs were obtained about 50 years ago, the methodology of their synthesis and their usage in chemistry and biochemical applications have begun to develop rapidly only in the last two decades. Due to the presence of spiro-function in the SNRs molecules, the latter have increased stability to various reducing agents (including biogenic ones), while the structures of

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Eastman, M. P., B. Freiha, C. C. Hsu, K. C. Lum, and C. Allen Chang. "Weak complexation of nitroxide radicals by cyclodextrins." Journal of Physical Chemistry 91, no. 7 (1987): 1953–56. http://dx.doi.org/10.1021/j100291a054.

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Gadányi, Szilvia, Tamás Kálai, József Jekö, Zoltán Berente, and Kálmán Hideg. "Synthesis of 2-Substituted Pyrrolidine Nitroxide Radicals." Synthesis 2000, no. 14 (2000): 2039–46. http://dx.doi.org/10.1055/s-2000-8727.

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Eastman, Michael P., B. Freiha, C. C. Hsu, and C. Allen Chang. "Complexation of nitroxide radicals by .gamma.-cyclodextrin." Journal of Physical Chemistry 92, no. 6 (1988): 1682–85. http://dx.doi.org/10.1021/j100317a058.

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Bruni, Paolo, Carla Conti, and Giorgio Tosi. "FT-IR investigation on (stable) nitroxide radicals." Journal of Molecular Structure 408-409 (June 1997): 477–81. http://dx.doi.org/10.1016/s0022-2860(96)09475-6.

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Tarasov, Valery F., Ilya A. Shkrob, and Alexander D. Trifunac. "Spin-Polarized Nitroxide Radicals in Organic Glasses†." Journal of Physical Chemistry A 106, no. 19 (2002): 4838–45. http://dx.doi.org/10.1021/jp014406p.

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