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KMID : 1059519920360030446
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Journal of the Korean Chemical Society
1992 Volume.36 No. 3 p.446 ~ p.452
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Base Catalysed Hydrolysis of Aryl Phenylacetates
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Chung Duck-Young
Yoh Soo-Dong
Choi Jae-Hwan
Shim Kwnag-Taik
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Abstract
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The rates of hydrolysis of aryl phenylacetates have been measured in the presence of piperidine in 80% acetonitrile-20% water(v/v). For the electron withdrawing substituents of leaving group, the hydrolysis is catalyzed by a general base and the Hammett ρLG and Bronsted value β are 5.28 and -2.72 at 30℃, respectively. These high senstivities of Hammett and Bronsted values are E1cB mechanism. But in the electron donating ones, the hydrolysis is catalyzed by a specific base and BAC2 mechanism is predominated. pKSH's of phenylacetic acid ester and rate constants of hydrolysis k1, k-1, k2 were calculated.
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