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Synthesis, characterization, spectroscopic and crystallographic investigation of metal complexes of N-benzyl-N-nitrosohydroxylamine

DOI: 10.4236/ojic.2013.31001    4,131 Downloads   8,528 Views   Citations

ABSTRACT

New metal complexes of N-benzyl-N-nitrosohy-droxylamine (BNHA) are isolated and characterized by elemental analysis, IR and UV-VIS spectroscopy. Spectrophotometric titration of aqueous solutions of BNHА by salts of some transition metals allowed to calculate the composition and formation constants of the metal complexes. The crystal structure of Cu (BNHА)2 is studied by X-ray diffraction. The Cu atom is coordinated by four O atoms of two bidentate ligands, which close 5-membered chelate rings. The N-O (1.306 ? - 1.320 ?) and N-N (1.274 ? and 1.275? ) bond lengths indicate that π electrons are delocalized over the chelating groups. Complexes form stacks with intermolecular Cu…N contacts equal to 3.118 ? and 3.306 ?.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

Kovalchukova, O. , Bostanabad, A. , Sergienko, V. , Polyakova, I. , Zyuzin, I. and Strashnova, S. (2013) Synthesis, characterization, spectroscopic and crystallographic investigation of metal complexes of N-benzyl-N-nitrosohydroxylamine. Open Journal of Inorganic Chemistry, 3, 1-6. doi: 10.4236/ojic.2013.31001.

References

[1] Buscarron, F. and Canela, J. (1974) Analytical uses of some n-nitroso-n-alkyl (or -n-cyclo-alkyl)hydroxylamines: Part II. Solvent extraction of metal hexahydrocupferrates. Analytica Chimica Acta, 70, 113-120. doi:10.1016/S0003-2670(01)82916-0
[2] Buscarron, F. and Canela, J. (1974) Analytical uses of some N-nitroso-N-alkyI (or -N-cycloalkyl)-hydroxylamines: Part III. N-Nitroso-N-cycIooctylhydroxylamine, N-nitroso-N-cyclododecylhydroxyl-amine and N-nitroso-N-isopropylhydroxylamine. Analytica Chimica Acta, 71, 468-471. doi:10.1016/S0003-2670(01)85455-6
[3] Brown, J. (1917) The use of cupferron (phenylnitrosohydroxylamine ammonium) in: I. The qantitative separation of zirconium, titanium, iron, manganese and aluminum. II. The analysis of zircon and baddeleytte. Journal of the American Chemical Society, 39, 2358-2366. doi:10.1021/ja02256a013
[4] Párkányi, L., Kálmán, A., Deák, A., Venter, M. and Haiduc, I. (1999) A new inorganic (carbon-free) chelate ring: SnO2N2. Eight-coordinated tin (IV) in Sn(O2N2Ph)4 and a self-assembled 20-membered macrocycle in [Me3Sn(O2N2Ph)]4. Inorganic Chemistry Communications, 2, 265-268. doi:10.1016/S1387-7003(99)00062-3
[5] Abraham, M.H., Bullock, J.I., Garland, J.H.N., Golder, A.J., Harden, G.J., Larkworthy, L.F., Povey, D.C., Riedl, M.J. and Smith, G.W. (1987) Copper and iron(III) complexes of N-nitroso-N-alkyl hydroxylamines, and the X-Ray crystal structures of bis(N-nitroso N-isopropylhydroxylaminato) copper(II) and tris(N-nitroso-N-isopropyl hydroxylaminato) iron(III). Polyhedron, 6, 1375-1381. doi:10.1016/S0277-5387(00)80898-0
[6] Basson, S.S., Ledipoldt, J.G., Roodt, A. and Venter, J.A. (1992) Structure of carbonyl(N-hydroxy-N-nitrosobenzenaminato-O,O’)(4-methyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2] octane)rhodium(I). Acta Crystallographica Section C, 48, 171-173. doi:10.1107/S0108270191008223
[7] Ahmed, M., Edwards, A.J., Jones, C.J., McCIeverty, J.A., Rothin, A.S. and Tate, J.P. (1988) Metal complexes of N-aryl-N-nitrosohydroxylamines: Cleavage of N-N bonds to give metal nitrosyl species and organonitrogen compounds, and the crystal structure of [RhCl2{ONN(C6H4Me-p)O} (H2O)(PPh3)]?0.5Me2CO. Journal of the Chemical Society, Dalton Transactions, 257-263 doi:10.1039/dt9880000257
[8] Najafi,, E., Amini, M.M. and Ng, S.W. (2011) Bis (?-Nnitroso-N-phenylhydroxylaminato)-?3O,O’:O’; ?3O’:O,O’bis[(Nnitroso-N-phenylhydroxylaminato-?2O,O’)lead(II)]. Acta Crystallographica Section E, 67, m377. doi:10.1107/S1600536811006775
[9] Najafi,, E., Amini, M.M. and Ng, S.W. (2011) Bis(N-nitroso-N-phenylhydroxylaminato-?2O,O’)(1,10-phenanthroline-?2N,N’)lead(II). Acta Crystallographica Section E, 67, m378. doi:10.1107/S1600536811006787
[10] Tamaki, K. and Okabe, N. (1998) Diaquabis[N-(1-naphthyl)- N-nitrosohydroxylaminato-O,O’]cobalt(II). Acta Crystallographica Section C, 54, 195-197. doi:10.1107/S0108270197013620
[11] Okabe, N. and Tamaki, K. (1995) Dimethanolbis(N-nitroso-N-phenylhydroxylaminato-O,O’)nickel(II). Acta Crystallographica Section C, 51, 2004-2005. doi:10.1107/S0108270195005816
[12] Van der Helm, D., Merritt Jr., L.L., Degeilh, R. and MacGillavry, C.H. (1965) The crystal structure of iron cupferron Fe(O2N2C6H5)3. Acta Crystallographica, 18, 355-362. doi:10.1107/S0365110X65000816
[13] Bolboaca, M., C?nt? S., Venter, M., Deak, A., Haiduc, I., Cozar, O., Iliescu, T., R?sch, P. and Kiefer, W. (2000) Vibrational behavior of transition metal cupferronato complexes: Raman studies on cobalt(II) cupferronato derivatives. Spectroscopy Letters, 33, 857-865. doi:10.1080/00387010009350162
[14] Pavel, I., C?nt? S., Venter, M., Deak, A., Haiduc, I., R?sch, P., Cozar, O. and Kiefer, W. (2000) Vibrational behavior of transition metal cupferronato complexes. Raman and SERS studies on nickel(II) cupferronato complexes. Vibrational Spectroscopy, 23, 71-76. doi:10.1016/S0924-2031(99)00086-7
[15] Tamaki, K. and Okabe, N. (1996) Manganese cupferronate. Acta Crystallographica Section C, 52, 1612-1614. doi:10.1107/S0108270196002661
[16] McGill, A.D., Zhang, W., Wittbrodt, J., Wang, J., Schlegel, H.B. and Wang, P.G. (2000) Para-Substituted N-Nitroso-N-oxybenzenamine ammonium salts: A new class of redox-sensitive nitric oxide releasing compounds. Bioorganic & Medicinal Chemistry, 8, 405-412. doi:10.1016/S0968-0896(99)00300-4
[17] Shiino, M., Watanabe, Y. and Umezawa, K. (2001) Synthesis of N-substituted N-nitrosohydroxylamines as inhibitors of Mushroom Tyrosinase. Bioorganic & Medicinal Chemistry, 9, 1233-1240. doi:10.1016/S0968-0896(01)00003-7
[18] Shiino, M., Watanabe, Y. and Umezawa, K. (2003) Synthesis and tyrosinase inhibitory activity of novel N-hydroxybenzyl-N-nitrosohydroxylamines. Bioorganic Chemistry, 31, 129-135. doi:10.1016/S0045-2068(03)00026-9
[19] Zyuzin, I.N., Nechiporenko, G.N., Golovina, N.I., Trofimova R.F., and Loginova, M.V. (1997) Synthesis and structure of di(non-azoxy) formals and some related N-alkyl-N’-alkoxydiazene N-oxides, Russian Chemical Bulletin, 46, 1421-1429. doi:10.1007/BF02505678
[20] Beck, M.T. and Nadypal, I. (1989) Chemistry of complex equilibria. Akad. Kiado, Budapest,
[21] APEX2 (Version 2008. 6-1), SAINT (V7.60A), SADABS (Version 2008/1), XPREP (Version 2008/2). (2005-2009) Bruker AXS Inc., Madison.
[22] Sheldrick G.M. (2008) A short history of SHELX. Acta Crystallographica Section A, 64, 112-122. doi:10.1107/S0108767307043930
[23] Thakur, N.V., Kartha, V.B., Kaneka, C.R. and Marthe, V.R. (1972) Infrared spectra of cupferron and some rare earth cupferrates, Journal of Inorganic and Nuclear Chemistry, 34, 2831-2836. doi:10.1016/0022-1902(72)80589-X
[24] Fochi, G., Floriani, C., Chiesi-Villa, A. and Guastini, C. (1986) Notes. Insertion of nitrogen oxide into a zirconium-carbon bond: Reaction of dialkylbis(cyclopentadienyl)zirconium(IV) complexes with nitrogen oxide. Journal of the Chemical Society, Dalton Transactions, 445-447. doi:10.1039/dt9860000445
[25] Allen, F.H., Kennard, O. and Taylor, R. (1983) Systematic analysis of structural data as a research technique in organic chemistry. Accounts of Chemical Research, 16, 146-153. doi:10.1021/ar00089a001

  
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