Add time:07/20/2019         Source:sciencedirect.com

The substitution of diethylzinc by phenylmercuric chloride is first order in each reactant, with k2 = 0.64 l·mole−1·sec−1 in solvent tetrahydrofuran, and with k2∼6 l·mole−1·sec−1 in solvent ether, both at 0°. The relative rate constants for substitution by phenylmercuric chloride in ether at 35° are Me2Zn(100), Et2Zn (450), Pr2Zn (1700), and iso-Pr2Zn (∼2200); this sequence is interpreted as arising from an SEi(SECi) mechanism of electrophilic substitution at saturated carbon. In solvent tetrahydrofuran at 25° the four dialkylzincs undergo substitution at approximately the same rate; this may be due to an exact balance of steric and polar effects in mechanism SEi, or to the displacement of co-ordinated tetrahydrofuran from the zinc atom by phenylmercuric chloride being, at least partly, rate-determining.

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