Abstract
The ambident behaviour of some reagents, NO2–, SCN– and ambident bases, in liquid solutions can be accounted for, quantitatively, in terms of the intersecting-state model. For many reactions changes in reactivity are dominated by the reaction energy, ΔG°, and the transition state bond order, n‡. A gain in polarity of the reactive bonds during the course of reaction leads to more negative ΔG° and to a decrease in n‡. This reveals that for the reaction energy barrier, ΔG° and n‡ can work in opposite directions as a function of the electronegativity of the reaction sites and be responsible for ambident behaviour in ‘charge control’ reactions (ΔG°) and ‘frontier-orbital control’ reactions (n‡). These concepts are employed to interpret the role of reagent, solvent, cation, and reaction mechanism on ambident reactivity.
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