Abstract
In a previous paper, it was determined from spectroscopic measurements that 1,1,1-trifluoro-3-(2-thenoyl)acetone (TTeA) was less than 2% enolized in water; the presence of cationic micelles did not increase the enol content, but a strong increase of its acid character was observed; e.g., in 0.02 M tetradecyltrimethylammonium bromide (TTABr), the measured pKa was nearly 3 u lower than that determined in water (Iglesias, E. Langmuir 2000, 16, 8438). In the present work, the nitrosation reaction of TTeA in both water and aqueous micellar solutions of the cationic surfactants TTABr and tetradecyltrimethylammonium chloride is studied. The reaction performed in water at low acidities (e.g., pH > 4) is extremely slow; conversely, in aqueous micellar solutions of cationic surfactants, the reaction is too slow at high acidities (e.g., pH < 2). Cationic micelles induce the nitrosation of TTeA at low acidities because of the rapid formation of enolate anions in the positively charged micellar interface. Rate enhance...
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