Abstract
This review article summarizes the electron transfer reactions of piperidine aminoxyl radicals. Electrochemical studies revealed the single electron transfer nature of piperidine aminoxyl radicals. In solution, piperidine aminoxyl radicals serve as single electron transfer oxidation reagent to react with various biologically interesting molecules such as glutathione, cysteine, ascorbic acid, and amines. The reaction product distribution, reaction kinetics, intermediates, and the reaction features in biological mimic environments including micelles and cyclodextrins were investigated. Oxoammonium salts, the one-electron transfer oxidation products of piperidine aminoxyl radicals, are agents of organic synthesis to selectively generate ketones or di-ketones from alcohols or ketones bearing α-methylene group under mild conditions. The new reactions of oxoammonium salts with aromatic amines, phenols, heterocycles including phenothiazines, papaverine, and bilirubin are also illustrated.
Similar content being viewed by others
References
Fukuzumi S. New perspective of electron transfer chemistry. Org Biomol Chem, 2003, 1: 609–620
Tuite E, Benniston A, Harriman A, et al. Electron transfer in chemistry. J Chem Soc, Perkin Trans 1, 2002, 17: 2028–2030
Mariano P S, ed. Advances in Electron Transfer Chemistry. Vol 6. Greenwich, C T: JAI Press, 1999
Eberson L. Electron-transfer reactions in organic chemistry. Adv Phys Org, 1982, 18: 79–185
Todres Z V. Ion-radical organic reactions. Tetrahedron, 1985, 41: 2771–2823
Liu Y C, Liu Z L. Free radical chemistry. Huaxue Tongbao, 1999, 12: 17–20
Liu Y C, Dang H S, Liu Z L. Some recent studies on electron transfer reactions at Lanzhou University. Rev Chem Intermed, 1986, 7: 111–131
Barclay L R C, Ingold K U. Autoxidation of biological molecules. 2. Autoxidation of a model membrane, comparison of the autoxidation of egg lecithin phosphatidylcholine in water and in chlorobenzene. J Am Chem Soc, 1981, 103: 6478–6785
Kehl H. Chemistry and Biology of Hydroxamic Acids. Basel: Karger, 1982
Soule B P, Hyodo F, Matsumoto K, et al. The chemistry and biology of nitroxide compounds. Free Radic Biol Med, 2007, 42: 1632–1650
Hideg K, Kalai T, Sar C P. Recent results in chemistry and biology of nitroxides. J Heterocycl Chem, 2005, 42: 437–450
Keana J F W. Newer aspects of the synthesis and chemistry of nitroxide spin labels. Chem Rev, 1978, 78: 37–64
Brik M E. Chemistry of persistent free bi- and polyradicals. Heterocycles, 1995, 41: 2827–2873
Naik N, Braslau R. Synthesis and applications of optically active nitroxides. Tetrahedron, 1998, 54: 667–696
Lemaire M T. Recent developments in the coordination chemistry of stable free radicals. Pure Appl Chem, 2004, 76: 277–293
Volodarsky L B, Reznikov V A, Ovcharenko V I. Synthetic chemistry of stable nitroxides. Boca Raton: CRC Press, 1994
Zhdanov R I. Bioactive Spin Labels. Berlin: Springer-Verlag, 1992
Berliner L J. Spin Labeling: The Next Millennium, Biological Magnetic Resonance, Vol 14. New York: Plenum Press, 1998
Hideg K, Hankovszky O H. Chemistry of spin-labeled amino acids and peptides, some new mono- and bifunctionalized nitroxide free radicals. Biol Magnetic Res, 1989, 8(Spin Labeling): 427–488
Kocherginsky N, Swartz H M. Nitroxide spin labels: Reactions in biology and chemistry. New York: CRC Press, 1995
Rozantsev E G. Nitroxyl radicals: Unique findings of 20th century Russian chemists. Rossiiskii Khimicheskii Zhurnal, 2000, 44: 87–91
Rozantsev E G, Sholle V D. Synthesis and reactions of stable nitroxyl radicals. II, reactions. Synthesis, 1971, 8: 401–414
Rozantsev E G, Sholle V D. Advances in the chemistry of nitroxyl radicals. Usp Khim, 1971, 40: 417–443
Rozantsev E G. Free Nitroxyl Radicals. New York: Plenum Press, 1970
Hoffman A K, Henderson A T. A new stable free radical: di-tert-Butylnitroxide. J Am Chem Soc, 1961, 83: 4671
Martinez de Ilarduya J I, Krzyczmonik P, Scholl H, et al. Electrode reactions of nitroxide radicals. IX, anodic oxidations of 4-hydroxyi-mino-2,2,6,6-tetramethylpiperidine-1-oxyl and 4-[(aminocarbonyl) hydrazone]-2,2,6,6-tetramethylpiperidine-1-oxyl in water solutions. Electroanalysis, 1991, 3: 233–237
Scholl H, Chmielewska B, Skowronski R, et al. Electrode reactions of nitroxyl radicals, derivatives of 2,2,6,6-tetramethylpiperidine. Part IV. Pol J Chem, 1987, 61: 851–859
Marx L, Schoellhorn B. Intramolecular charge effects in the electrochemical oxidation of aminoxyl radicals. New J Chem, 2006, 30: 430–434
Summermann W, Deffner U. Electrochemical oxidation of aliphatic nitroxyl radicals. Tetrahedron, 1975, 31: 593–596
Semmelhack M F, Chon C S, Cortes D A. Nitroxyl-mediated electrooxidation of alcohols to aldehydes and ketones. J Am Chem Soc, 1983, 105: 4492–4494
Andruzzi R, Trazza A, Greci L, et al. On the electrochemical reduction mechanism of indolinone nitroxide radicals in DMF. J Electroanal Chem Interfacial Electrochem, 1980, 107: 365–374
Neiman M B, Mairanovskii S G, Korvaraskaya B M, et al. Polarographic study of some N-oxide free radicals. Izv Akad Nauk SSSR, Ser Khim, 1964, 8: 1518–1521
Liu Y C, Zhang F, Jiang Z Q. Nitroxides, XVII, electrochemical behavior and kinetics of self-decay of piperidine nitroxide free radicals in aqueous solutions. Acta Chim Sin, 1987, 45: 447–483
Zhang F, Liu Y C. Studies on nitroxides, XVIII, kinetics of one- electron electrochemical oxidation of piperidine nitroxides in aqueous solution. Acta Chim Sin, 1989, 47: 186–190
Zhang F, Liu Y C. Studies on nitroxides, XXI, mechanism for the one-electron reduction electrode reaction of piperidine nitroxides in aqueous solution studied by polarography. Acta Chim Sin, 1989, 47: 1120–1123
Nicholson R S, Shain I. Theory of stationary electrode polarography, single scan and cyclic methods applied to reversible, irreversible, and kinetic systems. Anal Chem, 1964, 36: 706–723
Smith D E, McCord T G. Alternating current polarography and irreversible processes. Anal Chem, 1968, 40: 474–481
Galvez J, Molina A, Serna C. Pulse polarography. Part IX, method of discrimination between the catalytic, CF, ECE and EC mechanisms, calculation of the rate constants of the chemical reaction for the catalytic, CE and ECE mechanisms. J Electroanal Chem Interfacial Electrochem, 1981, 124: 201–211
Davydov R M. Interaction of iron (II) ions with an iminoxyl radical. Zh Fiz Khim, 1968, 42: 2639–2643
Medzhidov A A, Rozantsev E G, Neiman M B. Utilization of oxidizing properties of iminoxyl radicals for synthesis of individual ion-radicals from aromatic amines. Dokl Akad Nauk SSSR, 1966, 168: 348–350
Zelenin S N, Khidekel M L, Mozzhukhin D D, et al. Catalysis of hydrogen transfer by methods presumably similar to those of enzymes, III, model reactions of dihydronicotinamide-adenine dinucleotide coenzyme, effectiveness of flavines, quinones, and similar substances as catalysts. Zh Obshch Khim, 1967, 37: 1500–1507
Kalashnikova L A, Buchachenko A L, Neiman M B, et al. Energies of oxygen-hydrogen bond breaking in tri-tert-butylphenol and some hydroxylamines, and the strength of the π-complex of a dianisyl nitroxide radical with benzene. Zh Fiz Khim, 1969, 43: 64–71
Tatikolov A S, Khudyakov I V, Kuz’min V A. Kinetics of reactions of electron transfer between semiquinone and stable radicals. Izv Akad Nauk SSSR, Ser Khim, 1981, 5: 1003–1007
Liu Y C, Wu S P, Jiang Z Q, et al. Nitroxides, XI, one-electron transfer reaction of piperidine nitroxides with hydroxylamine. Chem J Chinese Univ, 1985, 6: 709–713
O’Neill P, Jenkins T C. Electron-transfer reactions of nitroxyl radicals with one-electron reduced quinones and viologens. J Chem Soc, Faraday Trans 1, 1979, 75: 1912–1918
Koroli L L, Kuzmin V A, Khudyakov I V. Kinetics of recombination, dismutation, and disproportionation reactions involving neutral ketyl radicals and radical anions. Int J Chem Kinet, 1984, 16: 379–396
Kaplan J, Canonico P G, Caspary W J. Electron spin resonance studies of spin-labeled mammalian cells by detection of surface-membrane signals. Proc Natl Acad Sci USA, 1973, 70: 66–70
Stier A, Sackmann E. Spin labels as enzyme substrates, heterogeneous lipid distribution in liver microsomal membranes. Biochim Biophys Acta, 1973, 311: 400–408
Lee T D, Birrell G B, Bjorkman P J, et al. Azethoxyl nitroxide spin labels, ESR studies involving thiourea crystals, model membrane systems and chromatophores, and chemical reduction with ascorbate and dithiothreitol. Biochim Biophys Acta, 1979, 550: 369–383
Chan T W, Bruice T C. Reaction of nitroxides with 1,5-dihydroflavins and N3,5-dimethyl-1,5-dihydrolumiflavin. J Am Chem Soc, 1977, 99: 7287–7291
Goldberg J S, Rauckman E J, Rosen G M. Bioreduction of nitroxides by Staphylococcus aureus. Biochem Biophys Res Commun, 1977, 79: 198–202
Kocherginsky N M, Kostetski Y Y, Smirnov A I. Use of nitroxide spin probes and electron paramagnetic resonance for assessing reducing power of beer, role of SH groups. J Agri Food Chem, 2005, 53: 1052–1057
Couet W R, Eriksson U G, Sosnovsky G, et al. Factors affecting nitroxide stability in biological materials. Biopharm Pharmacokinet Eur Congr, 2nd, 1984, 2: 616–625
Couet W R, Brasch R C, Sosnovsky G, et al. Factors affecting nitroxide reduction in ascorbate solution and tissue homogenates. Magn Reson Imaging, 1985, 3: 83–88
Giotta G J, Wang H H. Reduction of nitroxide free radicals by biological materials. Biochem Biophys Res Commun, 1972, 46: 1576–1580
Morrissett J D, Drott H R. Oxidation of the sulfhydryl and disulfide groups by the nitroxyl radical. J Biol Chem, 1969, 244: 5083–5084
Liu Y C, Wang X Z, Liu Z L. Studies on nitroxides, IV, oxidation of cysteine by 2,2,6,6-tetramethyl-4-hydroxypiperidine-1-oxyl. Chem J Chinese Univ, 1983, 4: 257–259
Liu Y C, Jiang Z Q, Zhang F. Nitroxides, XIII, mechanism of reaction between 2,2,6,6-tetramethyl-4-hydroxy-1-piperidinyloxy and d,l-cysteine in alkaline buffer solution. Acta Chim Sin, 1985, 43: 1086–1091
Liu Y C, Zhang F. Studies on nitroxides, XX, mechanistic study on reaction between 2,2,6,6-tetramethyl-4-hydroxypiperidine oxoammonium bromide and cysteine in acidic aqueous medium. Acta Chim Sin, 1989, 47: 411–416
Liu Y C, Jiang Z Q, Gao Z L. Studies on nitroxides, XIV, redox reaction of 2,2,6,6-tetramethyl-4-hydroxypiperidine nitroxide and glutathione. Chinese Sci Bull, 1987, 32: 286–287
Liu Y C, Gao Z L. Studies on nitroxides-kinetics and mechanism of the reaction tween glutathione and 2,2,6,6-tetramethyl-4-hydro-xypiperidine-1-oxyl radical in alkaline buffer. Chinese Sci Bull, 1988, 33: 2032–2035
Martinek K, Yatsimirski A K, Levashov A V, et al. The kinetic theory and the mechanisms of micellar effects on chemical reactions. In: Mittal K L, ed. Micellization, Solubilization, Microemulsions (Proc Int Symp). New York: Plenum Press, 1977. 489–508
Zhang F, Gao Z L, Liu Y C. Studies on single-electron oxidation of N-alkyl-p-phenylenediamines and benzidines in aqueous acetonitrile by cyclovoltammetry and ESR spectroscopy. Chem J Chin Univ, 1988, 4: 24–31
Gao Z L, Zhang F, Liu Y C. Studies on nitroxides, XXIII, single electron transfer reaction between piperidine nitroxide, its oxoammonium salt and N,N,N′,N′-tetramethyl-p-phenylenediamine in aqueous solution. Chem J Chinese Univ, 1989, 10: 718–723
Seib P A, Tolbert B M, ed. Ascorbic acid: Chemistry, metabolism, and uses. Advances in Chemistry Series, Vol 200. Washington DC: ACS, 1982
Craw M T, Depew M C. Contributions of electron spin resonance spectroscopy to the study of vitamins C, E and K. Rev Chem Intermed, 1985, 6: 1–31
Hubbell W L, McConnell H M. Motion of steroid spin labels in membranes. Proc Natl Acad Sci USA, 1969, 63: 16–22
Kocherginskii N M, Sakste N I, Berkovich M A, et al. Reduction of spin labels with ascorbic acid in solution and in biomembranes. Biofizika, 1981, 26: 442–446
Kornberg R D, McConnell H M. Inside-outside transitions of phospholipids in vesicle membranes. Biochem, 1971, 10: 1111–1120
Ross A H, McConnell H M. Permeation of a spin-label phosphate into the human erythrocyte. Biochem, 1975, 14: 2793–2798
Tonomura Y, Morales M F. Change in state of spin labels bound to sarcoplasmic reticulum with change in enzymic state, as deduced from ascorbate-quenching studies. Proc Natl Acad Sci USA, 1974, 71: 3687–3691
Quintanilha A T, Packer L. Surface localization of sites of reduction of nitroxide spin-labeled molecules in mitochondria. Proc Natl Acad Sci USA, 1977, 74: 570–574
Craescu C T, Baracu I, Grecu N, et al. On the reduction of nitroxide free radicals by ascorbic acid in solution and erythrocyte suspension. Rev Roum Biochim, 1982, 19: 15–23
Paleos C M, Dais P. Ready reduction of some nitroxide free radicals with ascorbic acid. J Chem Soc Chem Commun, 1977, 10: 345–346
Marx L, Chiarelli R, Guiberteau T, et al. A comparative study of the reduction by ascorbate of 1,1,3,3-tetraethylisoindolin-2-yloxyl and of 1,1,3,3-tetramethylisoindolin-2-yloxyl. J Chem Soc, Perkin Trans 1, 2000, 8: 1181–1182
Kocherginskii N M, Gol’dfel’d M G, Davydov R M, et al. Effect of detergents on the rate of reaction of iminoxyl radicals with ascorbic acid. Zh Fiz Khim, 1972, 46: 2375–2376
Lissi E A, Rubio M A, Araya D, et al. Reaction of di-tert-butyl nitroxide radicals. Int J Chem Kinet, 1980, 12: 871–881
Ebel C, Ingold K U, Michon J, et al. Nitroxides, 105, Kinetics of the reduction of a nitroxide radical by ascorbic acid in the presence of β-cyclodextrin. Tetrahedron Lett, 1985, 26: 741–744
Ebel C, Ingold K U, Michon J, et al. Nitroxides, 107, Kinetics of reduction of a nitroxide radical by ascorbic acid in the presence of β-cyclodextrin, determination of the radical β-cyclodextrin association constant and rate constants for reaction of the free and complexed nitroxide radical. Nouv J Chim, 1985, 9: 479–485
Okazaki M, Kuwata K. A stopped-flow ESR study on the reactivity of some nitroxide radicals with ascorbic acid in the presence of β-cyclodextrin. J Phys Chem, 1985, 89: 4437–4440
Liu Y C, Wu L M, Liu Z L, et al. Studies on nitroxides, XII, A kinetic ESR study on the oxidation of ascorbic acid by a nitroxide. Acta Chim Sin, 1985, 43: 669–674
Liu Y C, Liu Z L, Han Z X. Radical intermediates and antioxidant activity of ascorbic acid. Rev Chem Intermed, 1988, 10: 269–289
Doba T, Burton G W, Ingold K U. Antioxidant and co-antioxidant activity of vitamin C, the effect of vitamin C, either alone or in the presence of vitamin E or a water-soluble vitamin E analog, upon the peroxidation of aqueous multilamellar phospholipid liposomes. Biochim Biophys Acta, 1985, 835: 298–303
Niki E, Kawakami A, Yamamoto Y, et al. Oxidation of lipids, VIII, synergistic inhibition of oxidation of phosphatidylcholine liposome in aqueous dispersion by vitamin E and vitamin C. Bull Chem Soc Jpn, 1985, 58: 1971–1975
Pryor W A, Kaufman M J, Church D F. Autoxidation of micelle-solubilized linoleic acid, relative inhibitory efficiencies of ascorbate and ascorbyl palmitate. J Org Chem, 1985, 50: 281–283
Liu Y C, Han Z X, Wu L M, et al. Studies on bio-antioxidants-micellar effects on the reduction of nitroxides by vitamin C. Sci China Ser B, 1989, 32: 937–947
Liu Z L, Han Z X, Chen P, et al. Stopped-flow ESR study on the reactivity of vitamin E, vitamin C and its lipophilic derivatives towards Fremy’s salt in micellar systems. Chem Phys Lipids, 1990, 56: 73–80
Liu Z L, Han Z X, Chen P, et al. Studies on bio-antioxidants. II. An ESR study on the antioxidant efficiency of ascorbyl palmitate in micelles. Chin J Chem, 1991, 9: 144–155
Liu Y C, Liu Z L, Han Z X, et al. Microenvironmental effects on the reactivity of bioantioxidants. Prog Nat Sci, 1991, 1: 297–306
Wu L M, Guo F L, Liu Z L, et al. Antioxidant activity of lipophilic vitamin C derivative in dipalmitoyl phosphatidylcholine vesicles, a stopped-flow ESR kinetic study. Res Chem Intermed, 1993, 19: 657–668
Fendler E J, Fendler J H. Micellar catalysis in organic reactions: Kinetic and mechanistic implications. Adv Phys Org Chem, 1970, 8: 271–406
Burkey T J, Griller D. Micellar systems as devices for enhancing the lifetimes and concentrations of free radicals. J Am Chem Soc, 1985, 107: 246–249
Lei X G, Li Z Z, Liu Y C. Synthesis and properties of dialkylmethyl sulfate bilayers. J Chem Soc Chem Commun, 1990, 9: 711–712
Rozantsev E G, Neiman M B. Organic radical reactions involving no free valence. Tetrahedron, 1964, 20: 131–137
Liu Y C, Jiang Z Q. Studies on nitroxides, I, synthesis and reactions of piperidinyl nitroxides. Chem J Chinese Univ, 1980, 1: 71–79
Foster R. Organic Charge-Transfer Complexes. Organic Chemistry: A Series of Monographs, Vol 15. New York: Academic Press, 1969
Keute J S, Anderson D R, Koch T H. Photochemical reactivity of the di-tert-butyl nitroxide π,π* state and di-tert-butyl nitroxide halocarbon charge-transfer excited states. J Am Chem Soc, 1981, 103: 5434–5439
Jiang Z Q, Wu S P, Zhang M X, et al. Studies on nitroxides, XXII, contact charge transfer complexes of piperidine nitroxides with halomethanes and their photo-induced reactions. Chem J Chinese Univ, 1989, 10: 45–50
Merbouh N, Bobbitt J M, Brueckner C. Preparation of tetrameth-ylpiperidine-1-oxoammonium salts and their use as oxidants in organic chemistry, a review. Org Prep Proced Int, 2004, 36: 3–31
Merbouh N. 2,2,6,6-tetramethylpiperidine-based oxoammonium salts. Synlett, 2003, 11: 1757–1758
De Nooy A E J, Besemer A C, Van Bekkum H. On the use of stable organic nitroxyl radicals for the oxidation of primary and secondary alcohols. Synthesis, 1996, 10: 1153–1174
Pradhan P P, Bobbitt J M, Bailey W F. Novel reactions of oxoammonium salt with alkenes and activated aromatics. Abstracts, 35th Northeast Regional Meeting of the American Chemical Society, Binghamton, NY, United States, 2006
Merbouh N, Bobbitt J M, Brueckner C. Oxoammonium salts, 9, oxidative dimerization of polyfunctional primary alcohols to esters, an interesting β oxygen effect. J Org Chem, 2004, 69: 5116–5119
Yonekuta Y, Oyaizu K, Nishide H. Structural implication of oxoammonium cations for reversible organic one-electron redox reaction to nitroxide radicals. Chem Lett, 2007, 36: 866–867
Israeli A, Patt M, Oron M, et al. Kinetics and mechanism of the comproportionation reaction between oxoammonium cation and hydro xylamine derived from cyclic nitroxides. Free Radic Biol Med, 2005, 38: 317–324
Golubev V A, Rozantsev E G, Neiman M B. Some reactions of free iminoxyl radicals with unpaired electron participation. Izv Akad Nauk SSSR Ser Khim, 1965, 11: 1927–1936
Miyazawa T, Endo T, Shiikaski S, et al. Selective oxidation of alcohols by oxoaminium salts (R2N:O+X-). J Org Chem, 1985, 50: 1332–1334
Liu Y C, Liu Z L, Guo H X. Selective oxidation of secondary alcohols in the presence of primary alcohols by an oxoammonium salt. Chem J Chin Univ, 1988, 4: 90–94
Liu Y C, Guo H X, Liu Z L. Reactivity and selectivity in the oxidation of alcohols by oxoammonium salts. Acta Chim Sin, 1991, 49: 187–192
Guo H X, Liu Y C, Liu Z L, et al. 1-Oxo-2,2,6,6-tetramethyl-4-chloropiperidinium perchlorate. A new facile oxidant for phenol coupling. Res Chem Intermed, 1992, 17: 137–143
Liu Y C, Wang W, Guo Q X. Oxidative coupling of phenols by 2,2,6,6-tetramethyl-4-methoxypiperidine oxoammonium chloride. Chin Chem Lett, 1996, 7: 790–793
Bobbitt J H, Ma Z. Oxoammonium salts, 4, a new reagent for phenol coupling. Heterocycles, 1992, 33: 641–648
Mattay J, Runsink J. Additions of 1,1-diethoxyethene to 1,2-diketones. J Org Chem, 1985, 50: 2815–2818
Hills L R, Ronald R C. Total synthesis of (-)-grahamimycin A1. J Org Chem, 1985, 50: 470–473
Rozwadowska M D, Chrzanowska M. Synthetic entry into the secoisoquinoline alkaloids. Tetrahedron, 1985, 41: 2885–2890
Golubev V A, Miklyush R V. New preparative method for the oxidation of an activated methylene group to a carbonyl one. Zh Org Khim, 1972, 8: 1356–1357
Hunter D H, Barton D H R, Motherwell W J. Oxoammonium salts as oxidizing agents: 2,2,6,6-tetramethyl-1-oxopiperidinium chloride. Tetrahedron Lett, 1984, 25: 603–606
Liu Y C, Ren T, Guo Q X. Oxyfunctionalization of ketones bearing α-methylene group with piperidine oxoammonium salt, synthesis of α-diketones from monoketones. Chin J Chem, 1996, 14: 252–258
Ren T, Liu Y C, Guo Q X. Selective oxyfunctionalization of ketones using 1-oxopiperidinium salt. Bull Chem Soc Jpn, 1996, 69: 2935–2941
Bard A J, Ledwith A, Shine H J. Formation, properties and reactions of cation radicals in solution. Adv Phys Org Chem, 1976, 13: 155–278
Hammerich O, Parker V D. Kinetics and mechanisms of reactions of organic cation radicals in solution. Adv Phys Org Chem, 1984, 20, 55–189
Lewis G N, Lipkin D. Reversible photochemical processes in rigid media, the dissociation of organic molecules into radicals and ions. J Am Chem Soc, 1942, 64: 2801–2808
Walther B W, Williams F. ESR spectra and structure of the tetramethylsilane and tetramethylgermane radical cations. J Chem Soc, Chem Commun, 1982, 4: 270–272
Symons M C R. The radical cation of tetramethylstannane: An electron spin resonance study. J Chem Soc, Chem Commun, 1982, 15: 869–871
Liu Y C, Liu Z L, Chen P, et al. Generation of radical cations-a facile generation of radical cations via the action of an oxoammonium trifluoroacetate. Scientia Sinica, Series B, 1988, 31: 1062–1072
Liu Y C, Liu Z L, Wu L M, et al. A facile generation of radical cations via the action of nitroxides. Tetrahedron Lett, 1985, 26: 4201–4202
Abakumov G A, Tikhonov V D. Interaction of a stable radical of 2,2,6,6-tetramethyl-4-piperidone 1-oxide with acids. Izv Akad Nauk SSSR Ser Khim, 1969, 4: 796–801
Golubev V A, Zhdanov R I, Gida V M, et al. Interaction of iminoxyl radicals with some inorganic acids. Izv Akad Nauk SSSR Ser Khim, 1971, 4: 853–855
Golubev V A, Sen V D, Kulyk I V, et al. Mechanism of the acid disproportionation of di-tert-alkylnitroxyl radicals. Izv Akad Nauk SSSR, Ser Khim, 1975, 10: 2235–2243
Zheng X Q, Ruan X Q, Wang W, et al. Electron transfer between N-substituted phenothiazines and the 1-oxopiperidinium ion in the presence of β-cyclodextrin. Bull Chem Soc Jpn, 1999, 72: 253–257
Liu Y C, Ding Y B, Liu Z L. Preparation of single crystal and molecular structure of phenothiazine radical cation hexachloroantimonates. Acta Chim Sin, 1990, 48: 1199–1203
Wang Q G, Liu Y C, Ding Y B, et al. Crystal and molecular structure of N-methylphenothiazine radical cation hexachloroantimonate, MPT+SbCl6-. Jiegou Huaxue, 1988, 7: 153–156
Liu Y C, Ding Y B, Liu Z L, et al. Crystal and molecular structure of N-ethylphenothiazine radical cation hexachloroantimonate EPT+ SbCl −6 . Jiegou Huaxue, 1989, 8: 140–144
Uchida T, Ito M, Kozawa K. Crystal structure and related properties of phenothiazine cation radical-hexachloroantimonate, monoclinic(I) form. Bull Chem Soc Jpn, 1983, 56: 577–582
Ruperez F L, Conesa J C, Soria J, et al. X-ray diffraction and electron paramagnetic resonance study of chlorpromazine cation radical. J Phys Chem, 1985, 89: 1178–1181
Obata A, Yoshimori M, Yamada K, et al. Crystal and molecular structures of fenethazine hydrochloride and its cation radical-copper(II) complex salt. Bull Chem Soc Jpn, 1985, 58: 437–441
Apreda M C, Cano F H, Foces-Foces C, et al. Crystal and molecular structure of the alimemazine cation radical. J Chem Soc Perkin Trans 2, 1987, 5: 575–579
Kobayashi H. Crystal structure of an N-methylphenothiazine-7,7,8,8-tetracyanoquinodimethan complex. Bull Chem Soc Jpn, 1973, 46: 2945–2949
Guo Q X, Liu B, Liu Y C. ESR studies on N-alkylphenothiazine radical cation salts. Chem Res Chin Univ, 1995, 11: 195–201
Clarke D, Gilbert B C, Hanson P, et al. Heterocyclic free radicals, Part 8, the influence of the structure and the conformation of the side chain on the properties of phenothiazine cation-radicals substituted at nitrogen. J Chem Soc Perkin Trans 2, 1978, 10: 1103–1110
Gao X S, Feng J K, Jia Q, et al. Theoretical studies on the structures and electronic spectra of phenothiazine, N-methylphenothiazine and their radical cations. Acta Chim Sin, 1996, 54: 1159–1164
Li X S, Liu L, Mu T W, et al. A theoretical study on the structure and properties of phenothiazine derivatives and their radical cations. Res Chem Intermed, 2000, 26: 375–384
Zhang H M, Ruan X Q, Guo Q X, et al. A study on one-electron oxidation of phenothiazine derivatives by piperidine oxoammonium ion in SDS micelle. Res Chem Intermed, 1998, 24: 687–693
Guo Q X, Huan P, Liu B, et al. Chin Chem Lett, 1992, 3: 53–56
Liu L, Li X S, Mu T W, et al. Interplay between molecular recognition and redox properties: A theoretical study of the inclusion complexation of β-cyclodextrin with phenothiazine and its radical cation. J Inclusion Phenom Macrocyclic Chem, 2000, 38: 199–206
Fromherz P. Micelle structure: A surfactant block model. Chem Phys Lett, 1981, 77: 460–466
Dill K A, Flory P J. Molecular organization in micelles and vesicles. Proc Natl Acad Sci USA, 1981, 78: 676–680
Ruan X Q. M Sc. degree thesis. Lanzhou University, P. R. China, 1997
Marcus R A, Eyring H. Chemical and electrochemical electron-transfer theory. Ann Rev Phys Chem, 1964, 15: 155–196
Wu L M, Guo X, Wang J, et al. Kinetic studies on the single electron transfer reaction between 2,2,6,6-tetramethylpiperidine oxoammonium ions and phenothiazines: The application of Marcus theory. Sci China Ser B-Chem, 1999, 42: 138–144
Eberson L. Electron Transfer Reactions in Organic Chemistry. Berlin: Springer-Verlag, 1987
Kupchan S M, Liepa A J, Kameswaran V, et al. Novel nonphenol oxidative coupling. J Am Chem Soc, 1973, 95: 6861–6863
Hess U, Hiller K, Schroeder R, et al. Electrochemical rearrangement of papaverine and dimerization to 12,12′-bis{2,3,9,10-tetramethox-yindolo[2,1-a]isoquinolinyl}. J Prakt Chem, 1977, 319: 568–572
Ding Y B, Yang L, Liu Z L, et al. Novel oxidative coupling of papaverine by an oxoammonium salt. J Chem Res, 1994, 8: 328–329
Lightner D A, McDonagh A F. Molecular mechanisms of phototherapy for neonatal jaundice. Acc Chem Res, 1984, 17: 417–424
Schmid R, Mcdonagh A F. Hyperbilirubinemia. In: Stanbury J B, Wyngaarden J B, Fredrickson D S, eds. The Metabolic Basis of Inherited Diseases. 4th ed. New York: McGraw-Hill, 1978. 1221–1257
Stocker R, Yamamoto Y, McDonagh A F, et al. Bilirubin is an antioxidant of possible physiological importance. Science, 1987, 235: 1043–1046
Guo Q X, Yang L, Liu B, et al. A study on bilirubin radical cation generated by one-electron oxidation. Chem Res Chin Univ, 1992, 8: 301–304
Guo Q X, Wang J, Guo X, et al. Kinetics and mechanism of one-electron oxidation of bilirubin in dichloromethane solution. Res Chem Intermed, 1996, 22: 23–29
Liu Y C, Liu Z L, Chen P, et al. Oxoammonium trifluoroacetate-a facile oxidant for the generation of radical cations. Physical Organic Chemistry 1986. A Collection of the Invited Lectures Presented at the 8th IUPAC Conference on Physical Organic Chemistry, Tokyo, Japan, 24–29 August, 1986. In: Kobayashi M ed. Studies in Organic Chemistry. Amsterdam: Elsevier, 1987, 31: 59–66
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Zhang, F., Liu, Y. Electron transfer reactions of piperidine aminoxyl radicals. Chin. Sci. Bull. 55, 2760–2783 (2010). https://doi.org/10.1007/s11434-010-3255-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11434-010-3255-8