Mechanisms for reactions of halogenated compounds. Part 2. Orienting effects of chlorine substituents in nucleophilic aromatic substitution. Chambers, R. D, Close, D., Musgrave, W K. R, Waterhouse, J. S, & Williams, D L. H Journal of the Chemical Society, Perkin Transactions 2, 1977. Publisher: The Royal Society of Chemistry
Mechanisms for reactions of halogenated compounds. Part 2. Orienting effects of chlorine substituents in nucleophilic aromatic substitution [link]Paper  doi  abstract   bibtex   
Rate constants and product analyses are provided for reactions of various chloropolyfluoropyridines with ammonia in dioxan–water (60: 40 v/v) at 25 °C. Comparison of these rate constants with the values for appropriate polyfluoropyridines allows the separate effects of chlorine atoms , , and to the reaction centre to be established. The activating influence of chlorine decreases in the series \textgreater \textgreater (86 : 24 : 6.9 relative to hydrogen atom at the same position). The rate constant ratios : for chlorine orfluorine at the same position are: 3 : 1, . 1 : 1, and . 2.6 : 1. These ratios have been measured for a number of different substitutions and are remarkably constant. The results help to explain the orientation and reactivity of nucleophilic substitution in polyhalogenoaromatic compounds.
@article{chambers_mechanisms_1977,
	title = {Mechanisms for reactions of halogenated compounds. {Part} 2. {Orienting} effects of chlorine substituents in nucleophilic aromatic substitution},
	issn = {0300-9580},
	url = {http://dx.doi.org/10.1039/P29770001774},
	doi = {10.1039/P29770001774},
	abstract = {Rate constants and product analyses are provided for reactions of various chloropolyfluoropyridines with ammonia in dioxan–water (60: 40 v/v) at 25 °C. Comparison of these rate constants with the values for appropriate polyfluoropyridines allows the separate effects of chlorine atoms , , and to the reaction centre to be established. The activating influence of chlorine decreases in the series {\textgreater} {\textgreater} (86 : 24 : 6.9 relative to hydrogen atom at the same position). The rate constant ratios : for chlorine orfluorine at the same position are: 3 : 1, . 1 : 1, and . 2.6 : 1. These ratios have been measured for a number of different substitutions and are remarkably constant. The results help to explain the orientation and reactivity of nucleophilic substitution in polyhalogenoaromatic compounds.},
	number = {13},
	journal = {Journal of the Chemical Society, Perkin Transactions 2},
	author = {Chambers, Richard D and Close, Deborah and Musgrave, W Kenneth R and Waterhouse, John S and Williams, D Lyn H},
	year = {1977},
	note = {Publisher: The Royal Society of Chemistry},
	pages = {1774--1778},
}

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