✦ LIBER ✦

Relative rates of nucleophilic reactions of benzyl carbocation formed in photolysis of benzyl chloride and benzyl acetate in aqueous solution

✍ Scribed by Soili Jaarinen; Jukka Niiranen; Jouko Koskikallio

Publisher: John Wiley and Sons
Year: 1985
Tongue: English
Weight: 325 KB
Volume: 17
Category: Article
ISSN: 0538-8066
DOI: 10.1002/kin.550170902

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✦ Synopsis

Benzyl chloride and benzyl acetate were photolyzed in 30% methanol-water mixtures (V/V) at 0°C. The photolysis produces benzyl carbocations that react with nucleophiles. The reaction products were analyzed by gas chromatography or liquid chromatography. From the amounts of products the relative values of rate constants of reactions of benzyl carbocation with nucleophiles N and water k(N)/k(H,O) were calculated. Benzyl carbocation reacts with I-, Br-, C1-, and Ac-ions with approximately diffusion-controlled rate. A value of 2.4 x 10' dm3 mol-' s-' for the rate constant k(H,O) and a lifetime of 0.7 ns were estimated for benzyl carbocation in the aqueous solution.

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