Thiohydantoins. XI Kinetic Studies of the Alkaline Hydrolysis of 1-Acyl-2-thiohydantoins
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1-Acyl-2-thiohydantoins ionize in alkaline solution (pK ∼ 7). In solutions more alkaline than pH > 11 they are rapidly hydrolyzed to 2-thiohydantoin and a carboxylic acid, by attack of a hydroxide ion on the conjugate base of the 1-acyl-2-thiohydantoin. Possible mechanisms to accord with the entropy of activation, which is less negative than usual for base-catalyzed amide hydrolyses, are discussed. 1-Benzoyl-2-thiohydantoin hydrolyzes more rapidly than 1-acetyl-2-thiohydantoin, possibly because the ground state of the former molecule is destabilized by steric effects.
1978 ◽
Vol 43
(21)
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pp. 4002-4006
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1982 ◽
pp. 1467
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1986 ◽
pp. 2045
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1972 ◽
Vol 45
(1)
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pp. 203-208
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