53497-48-6Relevant articles and documents
Carboxylic acid amide enols: Keto-enol/enolate interconversion of N-methylindoline-2-one and its 2-thione and 2-selone analogs in aqueous solution
Kresge, A. Jerry,Meng, Qingshui
, p. 1528 - 1536 (1999)
Carbon-acid ionization constants, Q(a)(K) (concentration quotiem at ionic strength = 0.10 M), were determined by spectrophotometric titration in aqueous solution for N- methylindoline-2-one, pQ(a)(K) = 15.70, N-methylindoline-2-thione, pQ(a)(K) = 8.93, and N-methylindoline-2-selone, pQ(a)(K) = 7.25. Rate profiles were also constructed for the thione and selone. These were interpreted, with support from the form of acid-base catalysis as well as solvent and substrate isotope effects, as representing keto - enol/enolate ion interconversion. That led to the enol acidity constant pQ(a)(E) = 4.05 and the keto-enol equilibrium constant pK(E) = 4.88 for the thione and estimates of the limits on these quantities, pQ(a)(E) 4, for the selone.