Mechanisms for reactions of halogenated compounds. Part 3. Variation in activating influence of halogen substituents in nucleophilic aromatic substitution. Chambers, R. D, Close, D., & Williams, D L. H Journal of the Chemical Society, Perkin Transactions 2, 1980. Publisher: The Royal Society of Chemistry
Paper doi abstract bibtex Rate constants are reported for reactions of polyhalogeno-pyridines and -benzenes with sodium methoxide in methanol. Relative activating effects of individual fluorine and chlorine atoms at positions ,, and to the reaction site are determined and compared with orders determined from reactions involving ammonia in aqueous dioxan. The results are remarkably similar. Additional support is provided for earlier explanations of the activating effects of -fluorine and -chlorine. Activation parameters, determined for reactions of polyhalogenopyridines with ammonia in aqueous dioxan, clearly demonstrate that differences in reactivity along the series arise mainly from changes in activation energy.
@article{chambers_mechanisms_1980,
title = {Mechanisms for reactions of halogenated compounds. {Part} 3. {Variation} in activating influence of halogen substituents in nucleophilic aromatic substitution},
issn = {0300-9580},
url = {http://dx.doi.org/10.1039/P29800000778},
doi = {10.1039/P29800000778},
abstract = {Rate constants are reported for reactions of polyhalogeno-pyridines and -benzenes with sodium methoxide in methanol. Relative activating effects of individual fluorine and chlorine atoms at positions ,, and to the reaction site are determined and compared with orders determined from reactions involving ammonia in aqueous dioxan. The results are remarkably similar. Additional support is provided for earlier explanations of the activating effects of -fluorine and -chlorine. Activation parameters, determined for reactions of polyhalogenopyridines with ammonia in aqueous dioxan, clearly demonstrate that differences in reactivity along the series arise mainly from changes in activation energy.},
number = {5},
journal = {Journal of the Chemical Society, Perkin Transactions 2},
author = {Chambers, Richard D and Close, Deborah and Williams, D Lyn H},
year = {1980},
note = {Publisher: The Royal Society of Chemistry},
pages = {778--780},
}
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