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Abstract:

The reaction of [Ru(bpy)2(NO)Cl]2+ and [Fe(CN)5NO]2- with n-butylamine has been studied as a plausible route for obtaining aliphatic diazonium ions stabilized by coordination. These reactions yield a variety of products originating mainly by direct attack of nucleophiles on the intermediate carbocation (or diazonium ion) and by rearrangement of the carbocation or the diazonium ion. The ratio of unrearranged to rearranged products can be taken as an experimental measurement of the stabilization of the diazonium ions. DFT-computed results suggest that the stabilization by complexation of the diazonium ions is larger in the ironpentacyano complex, in agreement with the fact that no rearrangement products are observed in the reaction of this species with n-butylamine.

Registro:

Documento: Artículo
Título:Stabilization of aliphatic and aromatic diazonium ions by coordination: An experimental and theoretical study
Autor:Doctorovich, F.; Escola, N.; Trápani, C.; Estrin, D.A.; González Lebrero, M.C.; Turjanski, A.G.
Filiación:Depto. Quim. Inorg., Analitica Q., Universidad de Buenos Aires, Ciudad Universitaria, (1428) Buenos Aires, Argentina
Palabras clave:Amines; Complexation; Coordination reactions; Fourier transforms; Ions; Iron compounds; Ruthenium compounds; Aliphatic diazonium ions; Carbocation; Discrete Fourier transforms (DFT); Nucleophiles; Aromatic compounds
Año:2000
Volumen:19
Número:19
Página de inicio:3810
Página de fin:3817
DOI: http://dx.doi.org/10.1021/om000004c
Título revista:Organometallics
Título revista abreviado:Organometallics
ISSN:02767333
CODEN:ORGND
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02767333_v19_n19_p3810_Doctorovich

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Citas:

---------- APA ----------
Doctorovich, F., Escola, N., Trápani, C., Estrin, D.A., González Lebrero, M.C. & Turjanski, A.G. (2000) . Stabilization of aliphatic and aromatic diazonium ions by coordination: An experimental and theoretical study. Organometallics, 19(19), 3810-3817.
http://dx.doi.org/10.1021/om000004c
---------- CHICAGO ----------
Doctorovich, F., Escola, N., Trápani, C., Estrin, D.A., González Lebrero, M.C., Turjanski, A.G. "Stabilization of aliphatic and aromatic diazonium ions by coordination: An experimental and theoretical study" . Organometallics 19, no. 19 (2000) : 3810-3817.
http://dx.doi.org/10.1021/om000004c
---------- MLA ----------
Doctorovich, F., Escola, N., Trápani, C., Estrin, D.A., González Lebrero, M.C., Turjanski, A.G. "Stabilization of aliphatic and aromatic diazonium ions by coordination: An experimental and theoretical study" . Organometallics, vol. 19, no. 19, 2000, pp. 3810-3817.
http://dx.doi.org/10.1021/om000004c
---------- VANCOUVER ----------
Doctorovich, F., Escola, N., Trápani, C., Estrin, D.A., González Lebrero, M.C., Turjanski, A.G. Stabilization of aliphatic and aromatic diazonium ions by coordination: An experimental and theoretical study. Organometallics. 2000;19(19):3810-3817.
http://dx.doi.org/10.1021/om000004c