Navegar

Colección

Datos Estadísticas

Artículo

La versión final de este artículo es de uso interno de la institución.
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

In the present work the formation of several primary aliphatic coordinated nitrosamines by reaction of the extremely reactive K[IrCl5(NO)] in acetonitrile solution with the corresponding amine is described. Complete characterization, including X-ray diffraction determinations for some examples, are reported, and experimental evidence of their stability. Density functional theory calculations (DFT) helped to understand the role of the coordination environment of these complexes and to support, with excellent correlation with the experimental data, the proposed reaction pathways and stability studies. Complexes containing the highly unstable primary nitrosamines as ligands are generally scarce, and moreover, to our knowledge, our group has recently reported the first examples of isolated primary nitrosamines coordinated to the metal center only through the NO moiety. © 2008 American Chemical Society.

Registro:

Documento: Artículo
Título:Synthesis, structure, and reactivity of aliphatic primary nitrosamines stabilized by coordination to [IrCI5]2-
Autor:Di Salvo, F.; Estrin, D.A.; Leitus, G.; Doctorovich, F.
Filiación:Departamento de Quimica Inorganica, Analitica y Quimica Fisica/INQUIMAE-CONICET, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón II, piso 3, C1428EHA Buenos Aires, Argentina
Department of Chemical Services, Weizmann Institute of Science, Rehovot 76100, Israel
Palabras clave:Acetonitrile; Chemical reactivity; Coordination reactions; Iridium compounds; Ligands; Synthesis (chemical); X ray diffraction; Aliphatic coordinated nitrosamines; Primary nitrosamines; Amines
Año:2008
Volumen:27
Número:9
Página de inicio:1985
Página de fin:1995
DOI: http://dx.doi.org/10.1021/om700985h
Título revista:Organometallics
Título revista abreviado:Organometallics
ISSN:02767333
CODEN:ORGND
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02767333_v27_n9_p1985_DiSalvo

Referencias:

  • Magee, P.N., Barnes, J.M., (1956) Br. J. Cancer, 10, p. 114
  • These agents include N2O4, ClNO, BuONO, NO +, and acidified NO2- salts; see: Lee, J.; Chen, L.; West, A. H.; Richter-Addo, G. B. Chem. Rev. 2002, 102, 1019; Mirvish, S.S., (1975) Toxicol. Appl. Pharmacol, 31, p. 325
  • Ridd, J.H., (1961) Q. Rev. Chem. Soc, 15, p. 418
  • Hecht, S.S., (1998) Chem. Res. Toxicol, 11, pp. 1998-2560
  • Caulfield, J., Wishnok, J., Tannenbaum, S., (1998) J. Biol. Chem, 273 (21), p. 12689
  • Mohrig, J.R., Keegstra, K., (1967) J. Am. Chem. Soc, 89, p. 5492
  • Berner, D., McGarrity, J.F., (1979) J. Am. Chem. Soc, 101, p. 3135
  • Rayat, S., Wu, Z., Glaser, R., (2004) Chem. Res. Toxicol, 17, pp. 1998-1157
  • Glaser, R., Rayat, S., Lewis, M., Son, M., Meyer, S., (1999) J. Am. Chem. Soc, 121, pp. 6108-6119. , and references therein
  • Suzuki, T., Nakamura, T., Yamada, M., Ide, H., Kanaori, K., Tajima, K., Morii, T., Makino, K., (1999) Biochemistry, 38, p. 7151
  • Patai, S., (1978) The Chemistry of Diazonium and Diazo Groups, , Wiley: New York
  • Doctorovich, F., Trápani, C., (1999) Tetrahedron Lett, 40, p. 4635
  • Doctorovich, F., Escola, N., Trápani, C., Estrin, D.A., Turjansky, A.G., González Lebrero, M.C., (2000) Organometallics, 19, p. 3810
  • Doctorovich, F., Granara, M., Di Salvo, F., (2001) Transition Met. Chem, 26, p. 505
  • Trápani, C., Escola, N., Doctorovich, F., (2002) Organometallics, 21 (10), pp. 2021-2023
  • Di Salvo, F., Crespo, A., Estrin, D.A., Doctorovich, F., (2002) Tetrahedron, 58, p. 4237
  • Bowden, W.L., Little, W.F., Meyer, T.J., (1977) J. Am. Chem. Soc, 99, p. 4340
  • Doctorovich, F., Di Salvo, F., Escola, N., Trápani, C., Shimon, L., (2005) Organometallics, 24, p. 4707
  • Schramm, K., Schramm, D., Ibers, J.A., (1978) J. Am. Chem. Soc, 100, p. 2932
  • Keefer, L.K., Wang, S., Anjo, T., Fanning, J.C., Day, C.S., (1988) J. Am. Chem. Soc, 110, p. 2800
  • Vaughan, G.A., Chadwick, D.S., Hillhouse, G.L., (1989) J. Am. Chem. Soc, 111, pp. 5491-5493
  • Lalor, F.J., Desmond, T.J., Ferguson, G., Siew, P.Y., (1981) J. Chem. Soc., Dalton Trans, 1982, p. 10
  • Di Salvo, F., Escola, N., Estrin, D.A., Sherlis, D.A., Shimon, L., Doctorovich, F., (2007) Chem.-Eur. J, 13, p. 8428
  • Doctorovich, F., Di Salvo, F., (2007) Acc. Chem. Res, 40, p. 985
  • Fish, R.H., Jaouen, G., (2003) Organometallics, 22, p. 2166
  • Perissinotti, L.L., Estrin, D.A., Leitus, G., Doctorovich, F., (2006) J. Am. Chem. Soc, 128, p. 2512
  • Escola, N., Llebaria, A., Doctorovich, F., Leitus, G., (2006) Organometallics, 25, p. 3799
  • Escola, N., Di Salvo, F., Haddad, R., Perissinotti, L., Nogueira Eberlin, M., Doctorovich, F., (2007) Inorg. Chem, 46, p. 4827
  • Bottomley, F., Clarkson, S.G., Tong, S.B., (1974) J. Chem. Soc., Dalton Trans, 21, p. 2344
  • Bunton, C.A., Wolfe, B.B., (1974) J. Am. Chem. Soc, 96, p. 7747
  • Frisch, M. J, Tracks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Zakrzewski, V. G, Montgomery, J. A, Jr, Stratmann, R, Burant, J, Dapprich, S, Millam, J. M, Daniels, A. D, Kudin, K. N, Strain, M. C, Farkas, O, Tomasi, J, Barone, V, Cossi, M, Cammi, R, Mennucci, B, Pomelli, C, Adamo, C, Clifford, S, Ochterski, J, Petersson, G. A, Ayala, P. Y, Cui, Q, Morokuma, K, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Cioslowski, J, Ortiz, J. V, Baboul, A. G, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Gomperts, R, Martin, R. L, Fox, D. J, Keith, T, Al-Laham, M. A, Peng, C. Y, Nanayakkara, A, Gonzalez, C, Challacombe, M, Gill, P. M. W, Johnson, B, Chen, W, Wong, M. W, Andres, J. L, Gonzalez, C, Head-Gordon, M, Replogle, E. S, Pople, J. A. Gaussian 98, Rev. A7; Gaussian, Inc, Pittsburgh, PA, 1998; Becke, A.D., (1988) J. Chem. Phys, 98, p. 5648
  • Lee, C., Yang, W., Parr, R., (1998) Phys. Rev. B, 37, p. 785
  • Becke, A.D., (1998) Phys. Rev. A, 38, p. 3098
  • Godbout, N., Salahub, D.R., Andzelm, J., Wimmer, E., (1992) Can. J. Chem, 70, p. 560
  • Hay, P.J., Wadt, W.R., (1985) J. Chem. Phys, 82, p. 270
  • Wadt, W.R., (1985) J. Chem. Phys, 82, p. 299
  • Reed, A.E., Curtis, L.A., Weinhold, F., (1988) Chem. Rev, 88, p. 899
  • Cossi, M., Barone, V., Cammi, R., Tomasi, J., (1996) Chem. Phys. Lett, 255, p. 327
  • Ho, J., Fishbein, J.C., (1994) J. Am. Chem. Soc, 116, p. 6611
  • Lin-Vien, D., Colthup, N.B., Fateley, W.G., Grassetti, J.G., (1991) The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules; AP, Inc, p. 194. , San Diego, CA
  • Roberts, J.D., Chambers, V.C., (1951) J. Am. Chem. Soc, 73, p. 3176
  • E. J. Corey, E. J.; Atkinson, R. F. J. Org. Chem. 1964, 29, 3703; Finneman, J.I., Fishbein, J.C., (1996) J. Am. Chem. Soc, 118, p. 7134
  • These diazoalkanes were the only ones tested for deuterium incorporation by Fishbein et al. (refs 32 and 35)

Citas:

---------- APA ----------
Di Salvo, F., Estrin, D.A., Leitus, G. & Doctorovich, F. (2008) . Synthesis, structure, and reactivity of aliphatic primary nitrosamines stabilized by coordination to [IrCI5]2-. Organometallics, 27(9), 1985-1995.
http://dx.doi.org/10.1021/om700985h
---------- CHICAGO ----------
Di Salvo, F., Estrin, D.A., Leitus, G., Doctorovich, F. "Synthesis, structure, and reactivity of aliphatic primary nitrosamines stabilized by coordination to [IrCI5]2-" . Organometallics 27, no. 9 (2008) : 1985-1995.
http://dx.doi.org/10.1021/om700985h
---------- MLA ----------
Di Salvo, F., Estrin, D.A., Leitus, G., Doctorovich, F. "Synthesis, structure, and reactivity of aliphatic primary nitrosamines stabilized by coordination to [IrCI5]2-" . Organometallics, vol. 27, no. 9, 2008, pp. 1985-1995.
http://dx.doi.org/10.1021/om700985h
---------- VANCOUVER ----------
Di Salvo, F., Estrin, D.A., Leitus, G., Doctorovich, F. Synthesis, structure, and reactivity of aliphatic primary nitrosamines stabilized by coordination to [IrCI5]2-. Organometallics. 2008;27(9):1985-1995.
http://dx.doi.org/10.1021/om700985h