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2003 | 1 | 4 | 465-476
Tytuł artykułu

Hydrazyl, Nitronyl-, and imino-nitroxides: Synthesis, properties and reaction with nitric oxide and nitrogen dioxide

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Ten 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). The processes are easily monitored by UV-Vis or ESR spectroscopy.
Słowa kluczowe
Wydawca

Czasopismo
Rocznik
Tom
1
Numer
4
Strony
465-476
Opis fizyczny
Daty
wydano
2003-12-01
online
2003-12-01
Twórcy
  • Institute of Physical Chemistry, Spl. Independentei 202, 77208, Bucharest, Romania
autor
  • Institute of Physical Chemistry, Spl. Independentei 202, 77208, Bucharest, Romania
  • Institute of Physical Chemistry, Spl. Independentei 202, 77208, Bucharest, Romania
Bibliografia
  • [1] N. Hogg, R.J. Singh, J. Joseph, F. Neese, and B. Kalyanaraman: “Reactions of nitric oxide with nitronyl nitroxides and oxygen: prediction of nitrite and nitrate formation by kinetic simulation”, Free Rad. Res., Vol. 22, (1994), pp. 47–56. http://dx.doi.org/10.3109/10715769509147527[Crossref]
  • [2] T. Akaide, and M. Yoshida: “Antagonistic action of imidazolineoxyl N-oxides against endothelium-derived relaxing factor, no through a radical reaction”, Biochemistry, Vol. 32, (1993), pp. 827–832. http://dx.doi.org/10.1021/bi00054a013[Crossref]
  • [3] J. Joseph, B. Kalyanaraman and J.S. Hyde: “Trapping of nitrix-oxide by nitronyl nitroxides-an electron-spin-resonance investigation”, Biochem. Bioph. Res. Commun., Vol. 192, (1993), pp. 926–934. http://dx.doi.org/10.1006/bbrc.1993.1504[Crossref]
  • [4] G.M. Rosen, P. Tsai, and S. Pou: “Mechanism of free radical generation by nitric oxide synthase”, Chem. Rev., Vol. 102, (2002), pp. 1191–1199. http://dx.doi.org/10.1021/cr010187s[Crossref]
  • [5] P. Ionita, A.C. Whitwood, and B.C. Gilbert: “Synthesis and characterization of some novel hetero diradicals containing linked hydrazyl and aminoxyl (nitroxide) moieties”, J. Chem. Soc. Perkin Trans. 2, (2001), pp. 1453–1462. [Crossref]
  • [6] G. Ionita: “Reversed-phase TLC study of the interaction of some hydrazine derivatives with amino acids and BSA”, J. Planar Chromatogr., Vol. 12, (1999), pp. 421–424.
  • [7] G. Ionita, T. Constantinescu, and P. Ionita: “Normal and reversed phase TLC of some hydrazine derivatives”, J. Planar Chromatogr., Vol. 11, (1998), pp. 142–145.
  • [8] A. Caneschi, D. Gatteschi, and A. Lelirzin: “Crystal-structure and magneticproperties of a new ferrimagnetic chain containing manganese(ii) and a nitronylnitroxide radical-magnetic-ordering in mn (hfac) compounds”, J. Mater. Chem., Vol. 4, (1994), pp. 319–326. http://dx.doi.org/10.1039/jm9940400319[Crossref]
  • [9] C. Hansch, and A. Leo: “Substituents constants for correlation analysis in chemistry and biology”, Wiley, NY, 1979.
  • [10] C. Hirel, K.E. Vostrikova, J. Pecaut, V.I. Ovacharenko, and P. Rey: “Nitronyl and imino nitroxides: improvement of Ullman's procedure and report on a new efficient synthetic route”, Chem. Eur. J., Vol. 7, (2001), pp. 2007–2014. http://dx.doi.org/10.1002/1521-3765(20010504)7:9<2007::AID-CHEM2007>3.0.CO;2-7[Crossref]
  • [11] P.J. Thornally: “Theory and biological application of the ESR technique of spintrapping”, Life Chem. Reports, Vol. 4, (1986), pp. 57–112.
  • [12] G.R. Buettner: “Spin-trapping: ESR parameters of spin-adducts”, Free Rad. Bio. Med., (1987), pp. 259–303.
  • [13] V. Barone, A. Bencini, M. Cossi, A. Matteo, M. Mattesini, and F. Totti: “Assessment of a combined QM/MM aproach for the study of large nitroxide systems in vacuo and in condensed phases”, J. Am. Chem. Soc., Vol. 120, (1998), pp. 7069–7078. http://dx.doi.org/10.1021/ja981079z[Crossref]
  • [14] S.F. Nelsen: “Use of semi empirical AM1 calculations for the prediction of proton electron spin resonance spectra”, J. Chem. Soc. Perkin Trans., 2, (1998), pp. 1005–1008.
  • [15] W.B. Gleason, and R.E. Barnett: “Use of dipole approximation for nitroxide biradicals”, J. Am. Chem. Soc., Vol. 98, (1976), pp. 2701–2705. http://dx.doi.org/10.1021/ja00426a003[Crossref]
  • [16] P. Ionita, M.T. Caproiu, and A.T. Balaban: “New sulfonyl derivatives of DPPH and their complexes with crown ethers”, Rev. Roum. Chim., Vol. 45, (2000), pp. 935–941.
  • [17] T. Constantinescu, A. Mischie, O. Maior, F. Badea, M. Vasilescu, M.T. Caproiu, R. Socoteanu, and D. Nourescu: “New fluorescent derivatives of phenoxathiin. Synthesis and properties”, Rev. Roum. Chim., Vol. 45, (2000), pp. 1009–1117.
  • [18] K. Nakatani, and P. Yu: “Photocromic magnetic materials”, Adv. Mat., Vol. 13, (2001), pp. 1411–1413. http://dx.doi.org/10.1002/1521-4095(200109)13:18<1411::AID-ADMA1411>3.0.CO;2-Y[Crossref]
  • [19] S. Nakatsugi: “Organic multifunctional spin systems based on aminoxyl radicals”, Adv. Mat., Vol. 13, (2001), pp. 1719–1724. http://dx.doi.org/10.1002/1521-4095(200111)13:22<1719::AID-ADMA1719>3.0.CO;2-D[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_BF02475228
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