3545-74-2Relevant academic research and scientific papers
Micellar Effects upon the Hydrolysis of Activated Amides. Mechanistic Aspects
Cipiciani, Antonio,Linda, Paolo,Savelli, Gianfranco,Bunton, Clifford A.
, p. 5262 - 5267 (2007/10/02)
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.
