Mechanisms for reactions of halogenated compounds. Part 4.[1] activating influences of ring-nitrogen and trifluoromethyl in nucleophilic aromatic substitution

…, JS Waterhouse, DLH Williams, B Anderson

Index: Chambers, R. D.; Martin, P. A.; Waterhouse, J. S.; Williams, D. L. H.; Anderson, B. Journal of Fluorine Chemistry, 1982 , vol. 20, p. 507 - 514

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Citation Number: 33

Abstract

Abstract Rate constants have been measured for the reactions of ammonia with various fluorinated pyridines and diazines in aqueous dioxan at 25. From the results the activating effects of ring-nitrogen (relative to C H) and of trifluoromethyl (relative to-H) have been determined. Ring-nitrogen activates the system at points ortho-, meta-and para-to the point of substitution, in the ratios ortho-6.2× 10 4, meta-8.5× 10 2, and para-2.3× 10 5. Similarly ...