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.
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