Journal of the American Chemical Society

Reaction mechanism from structure-energy relations. 1. Base-catalyzed addition of alcohols to formaldehyde

E Grunwald

Index: Grunwald, Ernest Journal of the American Chemical Society, 1985 , vol. 107, # 16 p. 4710 - 4715

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Citation Number: 21

Abstract

Abstract: There is long-standing evidence that in the general base catalyzed addition of alcohols to formaldehyde, C.-0 bond formation and proton transfer occur simultaneously. Structure-energy relations for this reaction are complicated. The slopes of Br~ nsted plots vary greatly, even for structurally similar alcohols, and plots of log k vs. pK, of the alcohols go through minima. The data thus provide good material for testing the author's recent theory ...