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Tishkov, Alexander A.; Schmidhammer, Uli; Roth, S.; Riedle, Eberhard ORCID logoORCID: https://orcid.org/0000-0002-2672-5718 und Mayr, H. (2005): Ambident reactivity of the nitrite ion revisited. In: Angewandte Chemie International Edition, Bd. 44, Nr. 29: S. 4623-4626

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Abstract

Lost control: The rationalization of the ambident reactivity of NO2− by the change between charge control to orbital control has to be revised. SN1‐type reactions of carbocations with NO2− give kinetically controlled product mixtures only when these reactions proceed without activation energy (diffusion control). Activation‐controlled SN1 alkylations are reversible and lead to the thermodynamically more stable nitro compounds.

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