Abstract
The problem posed in the heading is a fundamental one and thus difficult to answer definitively. Provided the reader has become convinced that there exists such a thing as an outer-sphere ET mechanism (remember that this depends on a definition of outer-sphere ET as occurring via a transition state with maximally 1 kcal mol-1 (4 kJmol-1) of electronic interaction between the reactants) the problem can be given a distinct formulation: Are our elementary reactions — defined as reactions which so far have been formulated with one transition state only — really elementary, or do we have reason to write them in two steps, the initial one being of outer-sphere ET type? A clearcut case, to be discussed in more detail below (see Sect. XI.2.b) is the reaction between benzene and nitronium ion, the archetype of a polar, single transition state step (Fig. 1).
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Eberson, L. (1987). ET and Polar Mechanisms; How Are They Connected?. In: Electron Transfer Reactions in Organic Chemistry. Reactivity and Structure Concepts in Organic Chemistry, vol 25. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-72544-9_11
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