Journal of the American Chemical Society

Nucleophilic reactivity toward acetyl chloride in water

D Palling, WP Jencks

Index: Palling, David J.; Jencks, William P. Journal of the American Chemical Society, 1984 , vol. 106, # 17 p. 4869 - 4876

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Citation Number: 103

Abstract

Abstract: Rate constant ratios for the reactions of acetyl chloride with nucleophilic reagents in water containing 2.5%(v/v) dioxane were determined by product analysis. The rate constants show a small dependence on the basicity of primary amines, with p,,,= 0.25, and are assigned to rate-limiting attack of the nucleophile. Pyridines with pK,> 5 behave similarly, with p,,,= 0.24, but less basic pyridines react more slowly. Several" a-effect" ...

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