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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 16, Number 3
BKCSDE 16(3)
March 20, 1995 

Mechanistic Significances of the Reactivity-Selectivity Principle
Ikchoon Lee, Bon-Su Lee*, Han Joong Koh, Byung Doo Chang
The relationship between the signs of ρi(0), ρ j(0) and ρij and validity of the reactivity-selectivity principle (RSP) has been derived: RSP is valid when W = ρi(0)·ρj(0)/ρij is negative. The analysis of 100 reaction series indicated that for normal SN2 reactions involving variations of substituents in the nucleophile (X) and in the substrate (Y) RSP is valid only for a dissociative type for which ρY(0) is negative, whereas for the acyl transfer reactions with rate-limiting breakdown of the tetrahedral intermediate RSP is valid in general for all substituent changes, X, Y and/or Z (substituent on the leaving group). The trends in the validity of RSP for certain types of reaction can be useful in supplementing the mechanistic criteria based on the signs of ρi(0), ρj(0) and ρij.
277 - 281
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