- Micellar Effects upon the Hydrolysis of Activated Amides. Mechanistic Aspects
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Reactions of OH- in water with N-acylpyrrole, -indole, and -carbazole (acyl = acetyl or benzoyl) are second order in OH- in 10-3 M NaOH and first order in more concentrated OH-, but reaction in micelles of cetyltrimethylammonium bromide (CTABr) is first order in micellar-bound OH- for both 10-3 and 0.05 M NaOH.Reactions are inhibited by anionic micelles of sodium lauryl sulfate (NaLS).The rate-surfactant profiles for rate enhancements in CTABr, and inhibition in NaLS, are analyzed in terms of the distribution of OH- and amide between aqueous and micellar pseudophases: second-order rate constants for attack of OH- upon amide are lower in the micellar pseudophase than in water.Micellar effects upon reaction of OH- with anilides have been analyzed, giving second-order rate constants in the micellar pseudophase which are very similar to those in water.
- Cipiciani, Antonio,Linda, Paolo,Savelli, Gianfranco,Bunton, Clifford A.
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p. 5262 - 5267
(2007/10/02)
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