855229-58-2Relevant academic research and scientific papers
Ambident reactivity of the nitrite ion revisited
Tishkov, Alexander A.,Schmidhammer, Uli,Roth, Stefan,Riedle, Eberhard,Mayr, Herbert
, p. 4623 - 4626 (2005)
(Chemical Equation Presented) 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.
