Journal of the American Chemical Society

General-acid-catalyzed imidazolidine ring opening. Hydrolysis of symmetrical and unsymmetrical 1, 3-imidazolidines of p-dimethylaminocinnamaldehyde

TH Fife, AM Pellino

Index: Fife, Thomas H.; Pellino, August M. Journal of the American Chemical Society, 1980 , vol. 102, # 9 p. 3062 - 3071

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Citation Number: 16

Abstract

Abstract: Rate constants have been obtained for ring opening of a series of symmetrical and unsymmetrical 1, 3-imidazolidines of p-dimethylaminocinnamaldehyde in H2O at 30" C. Ring opening of the N, N'-diphenyl derivative is catalyzed by hydronium ion (k~= 2290 M-'sI), and gives rise to a cationic Schiff base with A, 505 nm. The reaction is considerably slower in D20 than in H20, kHjkD= 3.0. At pH greater than 6 ring opening is pH independent (ko'= ...