Mechanism of esterification of 1, 3-dimethylamino alcohols by N-acetylimidazole in acetonitrile and the influence of alkyl and geminal dialkyl substitution upon the rate

…, S Sebastian, D Van Haver, PJ De Clercq…

Index: Madder, Annemieke; Sebastian, Sonny; Van Haver, Dirk; De Clercq, Pierre J.; Maskill, Howard Journal of the Chemical Society. Perkin Transactions 2, 1997 , # 12 p. 2787 - 2793

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Abstract

3-(Dimethylamino) propan-1-ol and seven derivatives with alkyl substituents at the 2- position have been prepared by conventional methods, and second-order rate constants for their esterification by N-acetylimidazole in acetonitrile have been measured under pseudo- first-order conditions both by 1H NMR spectroscopy at a single temperature (23° C) and by a UV spectroscopic method over the temperature range 25–65° C. Evidence is presented ...