Thiohydantoins. X. Kinetic Studies of the Acid Hydrolysis of 1-Acyl-2-thiohydantoins

Thiohydantoins. X. Kinetic Studies of the Acid Hydrolysis of 1-Acyl-2-thiohydantoins

The rates of hydrolysis of 22 1-acyl-2-thiohydantoins in aqueous sulfuric acid to give 2-thiohydantoin and a carboxylic acid have been determined. In 0-90% sulfuric acid, hydrolysis takes place by an A-2 mechanism, and the rate reaches a maximum in about 70% acid. In acid more concentrated than abou...

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Veröffentlicht in:Canadian journal of chemistry 1972-12, Vol.50 (23), p.3767-3779
Hauptverfasser: Congdon, Wayne Irvine, Edward, John Thomas
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container_title Canadian journal of chemistry
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Edward, John Thomas
description The rates of hydrolysis of 22 1-acyl-2-thiohydantoins in aqueous sulfuric acid to give 2-thiohydantoin and a carboxylic acid have been determined. In 0-90% sulfuric acid, hydrolysis takes place by an A-2 mechanism, and the rate reaches a maximum in about 70% acid. In acid more concentrated than about 90%, hydrolysis takes place by an A-1 mechanism, and the rate increases monotonically. Evidence for the two mechanisms comes from Yates r and Bunnett-Olsen parameters; from entropies of activation; from pσ and pσ + relations; and from steric effects.
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title Thiohydantoins. X. Kinetic Studies of the Acid Hydrolysis of 1-Acyl-2-thiohydantoins
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