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Prof. Dr. Herbert Mayr, Dr. Martin Breugst and Dr. Armin R. Ofial Farewell to the HSAB Treatment of Ambident Reactivity Angewandte Chemie International Edition 50

Version of Record online: 1 JUL 2011 | DOI: 10.1002/anie.201007100

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Hard or soft? The prediction of ambident reactivity by the concept of hard and soft acids and bases fails in the majority of cases and has to be abandoned. In this Review an alternative approach is presented to rationalize the regioselectivities of ambident systems which differentiates between kinetic and thermodynamic product control as well as between reactions proceeding with and without activation energy. The predictive power of qualitative Marcus theory is demonstrated.

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