The limitations of the reactivity—selectivity principle (RSP) are discussed in terms of the qualitative configuration mixing (CM) model. It is concluded that the RSP is expected to break down for cases in which the reaction transition state takes on character largely absent in reactants or products, though not all breakdowns of the RSP are attributed to this cause. This conclusion is illustrated with two model reactions that do not follow the RSP: (a) radical addition to alkenes, and (b) nucleophilic aliphatic substitution. Analysis leads us to agree with previous statements by Jencks and Arnett that the RSP should be abandoned as a predictive tool.
|Number of pages||5|
|Journal||Israel Journal of Chemistry|
|State||Published - 1 Jan 1985|
ASJC Scopus subject areas
- Chemistry (all)