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 ChemistryPaper 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},
}
Downloads: 0
{"_id":"5wnyGdNK7DaQFchr8","bibbaseid":"chambers-close-musgrave-waterhouse-williams-mechanismsforreactionsofhalogenatedcompoundspart2orientingeffectsofchlorinesubstituentsinnucleophilicaromaticsubstitution-1977","author_short":["Chambers, R. D","Close, D.","Musgrave, W K. R","Waterhouse, J. S","Williams, D L. H"],"bibdata":{"bibtype":"article","type":"article","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":[{"propositions":[],"lastnames":["Chambers"],"firstnames":["Richard","D"],"suffixes":[]},{"propositions":[],"lastnames":["Close"],"firstnames":["Deborah"],"suffixes":[]},{"propositions":[],"lastnames":["Musgrave"],"firstnames":["W","Kenneth","R"],"suffixes":[]},{"propositions":[],"lastnames":["Waterhouse"],"firstnames":["John","S"],"suffixes":[]},{"propositions":[],"lastnames":["Williams"],"firstnames":["D","Lyn","H"],"suffixes":[]}],"year":"1977","note":"Publisher: The Royal Society of Chemistry","pages":"1774–1778","bibtex":"@article{chambers_mechanisms_1977,\n\ttitle = {Mechanisms for reactions of halogenated compounds. {Part} 2. {Orienting} effects of chlorine substituents in nucleophilic aromatic substitution},\n\tissn = {0300-9580},\n\turl = {http://dx.doi.org/10.1039/P29770001774},\n\tdoi = {10.1039/P29770001774},\n\tabstract = {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.},\n\tnumber = {13},\n\tjournal = {Journal of the Chemical Society, Perkin Transactions 2},\n\tauthor = {Chambers, Richard D and Close, Deborah and Musgrave, W Kenneth R and Waterhouse, John S and Williams, D Lyn H},\n\tyear = {1977},\n\tnote = {Publisher: The Royal Society of Chemistry},\n\tpages = {1774--1778},\n}\n\n","author_short":["Chambers, R. D","Close, D.","Musgrave, W K. R","Waterhouse, J. S","Williams, D L. H"],"key":"chambers_mechanisms_1977","id":"chambers_mechanisms_1977","bibbaseid":"chambers-close-musgrave-waterhouse-williams-mechanismsforreactionsofhalogenatedcompoundspart2orientingeffectsofchlorinesubstituentsinnucleophilicaromaticsubstitution-1977","role":"author","urls":{"Paper":"http://dx.doi.org/10.1039/P29770001774"},"metadata":{"authorlinks":{}},"html":""},"bibtype":"article","biburl":"https://bibbase.org/zotero/kjelljorner","dataSources":["64RFiGdCa5JLg5kLH"],"keywords":[],"search_terms":["mechanisms","reactions","halogenated","compounds","part","orienting","effects","chlorine","substituents","nucleophilic","aromatic","substitution","chambers","close","musgrave","waterhouse","williams"],"title":"Mechanisms for reactions of halogenated compounds. Part 2. Orienting effects of chlorine substituents in nucleophilic aromatic substitution","year":1977}