Limitations of the Reactivity—Selectivity Principle. Application to Free Radical Addition to Alkenes and Nucleophilic Aliphatic Substitution | Zendy

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Limitations of the Reactivity—Selectivity Principle. Application to Free Radical Addition to Alkenes and Nucleophilic Aliphatic Substitution

Author(s) -

Pross Addy

Publication year - 1985

Publication title -

israel journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.908

H-Index - 54

eISSN - 1869-5868

pISSN - 0021-2148

DOI - 10.1002/ijch.198500125

Subject(s) - chemistry , reactivity (psychology) , selectivity , nucleophile , nucleophilic substitution , computational chemistry , substitution (logic) , medicinal chemistry , photochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology , computer science , programming language

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.

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