Hydrolysis of Orthocarbonates. Evidence for Charge Imbalance in the Transition State for the General Acid Catalyzed Process
P Kandanarachchi, ML Sinnott
Index: Kandanarachchi, Pramod; Sinnott, Michael L. Journal of the American Chemical Society, 1994 , vol. 116, # 13 p. 5601 - 5606
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Abstract
Abstract: Catalytic constants have been measured for the hydrolysis of a range of aryl orthocarbonates, in which both the leaving group and trioxocarbenium ion moiety have been systematically varied, by neutral carboxylic acids (trichloroacetic, difluoroacetic, dichloroacetic, malonic, chloroacetic, and acetic) at 70.0 OC in 60% water-409b acetonitrile, I= 1. OM (KC1). Curvature cannot be detected in Brransted plots involving carboxylic acids ...
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