Abstract:
In this work we present for the first time an X-ray structure of a coordinated S-nitrosothiol obtained by reaction of the extremely reactive K[IrCl5NO] with benzylmercaptan in acetonitrile. This surprisingly stable compound, trans-K[IrCl4(CH3CN)N(O)SCH2Ph], was isolated in high yield (80%) and fully characterized by FTIR, 1H NMR, and ESI-MS. To our knowledge this is the first example of a coordinated S-nitrosothiol that has been isolated. Copyright © 2006 American Chemical Society.
Registro:
Documento: |
Artículo
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Título: | A surprisingly stable S-nitrosothiol complex |
Autor: | Perissinotti, L.L.; Estrin, D.A.; Leitus, G.; Doctorovich, F. |
Filiación: | Departamento de Quimica Inorganica, Analitica y Quimica Fisica/INQUIMAE-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, (C1428EHA) Buenos Aires, Argentina Department of Chemical Services, Weizmann Institute of Science, Rehovot 76100, Israel
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Palabras clave: | s nitrosothiol; article; complex formation; crystal structure; density functional theory; infrared spectroscopy; proton nuclear magnetic resonance; synthesis |
Año: | 2006
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Volumen: | 128
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Número: | 8
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Página de inicio: | 2512
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Página de fin: | 2513
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DOI: |
http://dx.doi.org/10.1021/ja0565976 |
Título revista: | Journal of the American Chemical Society
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Título revista abreviado: | J. Am. Chem. Soc.
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ISSN: | 00027863
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CODEN: | JACSA
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00027863_v128_n8_p2512_Perissinotti |
Referencias:
- Tasker, H.S., Jones, H.O., (1909) J. Chem. Soc., 95, p. 1910
- Mannick, J.B., Hausladen, A., Liu, L., Hess, D.T., Zeng, M., Miao, Q.X., Kane, L.S., Stamler, J.S., (1999) Science, 284, pp. 651-654
- Stamler, J.S., Jaraki, O., Osborne, J., Simon, D.I., Keaney, J., Vita, J., Singel, D., Loscalzo, J., (1992) Proc. Natl. Acad. Sci. U.S.A., 89, pp. 7674-7677
- Jourd'heuil, D., Hallén, K., Feelisch, M., Grisham, M.B., (2000) Free Radical Biol. Med., 28, pp. 409-417
- Arulsalmy, N., Dohle, D.S., Butt, J.A., Irvine, G.J., Jordan, P.A., Sagan, E., (1999) J. Am. Chem. Soc., 121, pp. 7115-7123
- Field, L., Dilts, R.V., Ravichandran, R., Lenhert, P.G., Carnahan, G.E., (1978) J. Chem. Soc., Chem. Commun., pp. 249-250
- Carnahan, G.E., Lenhert, P.G., Ravichandran, R., (1978) Acta Crystallogr., B34, pp. 2645-2648
- Goto, K., Hino, Y., Kawashima, T., Kaminaga, M., Yano, E., Yamamoto, G., Takagi, M., Nagase, S., (2000) Tetrahedron Lett., 41, pp. 8479-8483
- Bartberger, M.D., Houk, K.N., Powell, S.C., Mannion, J.D., Lo, K., Stamler, J.S., Toone, E.J., (2000) J. Am. Chem. Soc., 122, pp. 5889-5890
- Chan, N.L., Rogers, P.H., Armone, A., (1998) Biochemistry, 37, pp. 16459-16464
- Szacilowski, K., Stasicka, Z., (2000) Prog. React. Kinet. Mech., 6, pp. 1-58
- Morando, P.J., Borghi, E.B., Schteingart, L.M., Blesa, M.A., (1981) J. Chem. Soc., Dalton Trans., pp. 435-440
- Baraldo, L.M., Bessega, M.S., Rigotti, G.E., Olabe, J.A., (1994) Inorg. Chem., 33, pp. 5890-5896
- Ford, P.C., Lorkovic, I.M., (2002) Chem. Rev., 102 (4), pp. 993-1017
- Szacilowski, K., Wanat, A., Barbieri, A., Wasielewska, E., Witko, M., Stochel, G., Stasicka, Z., (2002) New J. Chem., 26, pp. 1495-1502
- Roncaroli, F., Olabe, J.A., (2005) Inorg. Chem., 44 (13), pp. 4719-4727
- Schwane, J.D., Ashby, M.T., (2002) J. Am. Chem. Soc., 124, pp. 6822-6823
- note; Frisch, M.J., (1998) Gaussian 98, Rev. A7, , Gaussian: Inc., Pittsburgh, PA
- Becke, A.D., (1988) Phys. Rev. A, 38, pp. 3098-3100
- Perdew, J.P., Wang, Y., (1992) Phys. Rev. B, 45, pp. 13244-13249
- Hay, P.J., Wadt, W.R., (1985) J. Chem. Phys., 82, pp. 299-310
- Grossi, L., Montevecchi, P.C., Strazzari, G., (2001) Eur. J. Org. Chem., pp. 131-135
- Oae, S., Kim, Y.H., Fukushima, D., Shinhama, K., (1978) J. Chem. Soc., Perkin Trans. 1, pp. 913-917
- Estrin, D.A., Baraldo, L.M., Barja, B.C., Olabe, J.A., Paglieri, L., Corongiu, G., (1996) Inorg. Chem., 35, pp. 3897-3903
Citas:
---------- APA ----------
Perissinotti, L.L., Estrin, D.A., Leitus, G. & Doctorovich, F.
(2006)
. A surprisingly stable S-nitrosothiol complex. Journal of the American Chemical Society, 128(8), 2512-2513.
http://dx.doi.org/10.1021/ja0565976---------- CHICAGO ----------
Perissinotti, L.L., Estrin, D.A., Leitus, G., Doctorovich, F.
"A surprisingly stable S-nitrosothiol complex"
. Journal of the American Chemical Society 128, no. 8
(2006) : 2512-2513.
http://dx.doi.org/10.1021/ja0565976---------- MLA ----------
Perissinotti, L.L., Estrin, D.A., Leitus, G., Doctorovich, F.
"A surprisingly stable S-nitrosothiol complex"
. Journal of the American Chemical Society, vol. 128, no. 8, 2006, pp. 2512-2513.
http://dx.doi.org/10.1021/ja0565976---------- VANCOUVER ----------
Perissinotti, L.L., Estrin, D.A., Leitus, G., Doctorovich, F. A surprisingly stable S-nitrosothiol complex. J. Am. Chem. Soc. 2006;128(8):2512-2513.
http://dx.doi.org/10.1021/ja0565976