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Nucleophilic Reactivities of Bleach Reagents

2018/05/09 by Robert J. Mayer, Armin R. Ofial · 1 citation
Chemistry · Environmental Science · #Chemical Reaction Mechanisms #Chemistry and Chemical Engineering #Chemical Synthesis and Reactions

paper · doi:10.1021/acs.orglett.8b00645

openalex publication_date 2018/05/09 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

The nucleophilicities of the oxidants hydroperoxide, hypochlorite, hypobromite, bromite, and peroxymonosulfate were determined by following the kinetics of their reactions with a series of benzhydrylium ions of known electrophilicity ( E ) in alkaline, aqueous solutions at 20 °C. The reactivities of the oxidants correlate only weakly with their basicities. Analyzing the rate constants by using the relationship log k 2 = s N ( N + E ) gave the parameters N (and s N ), which were applied to predict the rates of Weitz–Scheffer epoxidations.

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