Kinetics of electrophile-nucleophile combinations: A general approach to polar organic reactivity

Top Cited Papers

Open Access

1 January 2005

journal article
Published by Walter de Gruyter GmbH in Pure and Applied Chemistry

Vol. 77 (11) , 1807-1821
https://doi.org/10.1351/pac200577111807

Abstract

Benzhydrylium ions (Ar2CH+) and structurally related quinone methides are employed as reference electrophiles for comparing the nucleophilicities of a large variety of compounds, e.g., alkenes, arenes, alkynes, allylsilanes, allylstannanes, enol ethers, enamines, diazo compounds, carbanions, transition-metal π-complexes, hydride donors, phosphanes, amines, alkoxides, etc., using the correlation equation log k (20 °C) = s(N + E), where s and N are nucleophile-dependent parameters and E is an electrophilicity parameter. The same equation was employed to derive the electrophilicity parameter E for different types of carbocations, cationic transition-metal π-complexes, typical Michael acceptors, and electron-deficient arenes. The E, N, and s parameters thus obtained can be used for predicting rates and selectivities of polar organic reactions.

Keywords

This publication has 0 references indexed in Scilit: