THE ALKALINE HYDROLYSIS OF N-ACYLTHIOUREAS
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N-Benzoylthiourea (pKHA 10.9) and other N-acylthioureas ionize in alkaline solution, and then are rapidly hydrolyzed to thiourea and a carboxylic acid. The rates become independent of hydroxide ion concentration when this exceeds about 0.1 M and point to a mechanism in which hydrolysis takes place by attack of an hydroxide ion on the un-ionized molecule of N-acylthiourea. This mechanism accords with the Arrhenius parameters for the hydrolysis of N-benzoylthiourea in 0.2 N sodium hydroxide, and with the Hammett ρ value of 0.10 for the hydrolysis of m- and p-substituted N-benzoylthioureas in 1.0 N potassium hydroxide.
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1979 ◽
pp. 1093
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1967 ◽
pp. 1265
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1986 ◽
pp. 2045
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1968 ◽
pp. 548
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Keyword(s):
1978 ◽
Vol 43
(21)
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pp. 4002-4006
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