{"title":"Aromatic reactivity. Part XLVII. Effects of 10-substituents on the rates of detritiation at the 9-position of phenanthrene","authors":"C. Eaborn, A. Fischer, D. Killpack","doi":"10.1039/J29710002142","DOIUrl":null,"url":null,"abstract":"The rates of detritiation of some 10-X-[9-3H]phenanthrenes in anhydrous trifluoroacetic acid have been measured at several temperatures. The values of the rates, krel, at 70° relative to that for [9-3H]phenanthrene are (X =) Me, 180; F, 4·1; Cl, 0·185; Br, 0·11; I, 0·14. Change of temperature has a large effect on the activating influence of the methyl group, the values of krel being ∼420, ∼350, and 230 at 0, 25, and 50°, respectively. The relatively large activation by fluorine, and the order of deactivation by the other halogens point to a contribution from resonance effects relative to those from inductive effects which is unusually high for ortho-substituents.","PeriodicalId":17268,"journal":{"name":"Journal of The Chemical Society B: Physical Organic","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"2","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of The Chemical Society B: Physical Organic","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1039/J29710002142","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 2
Abstract
The rates of detritiation of some 10-X-[9-3H]phenanthrenes in anhydrous trifluoroacetic acid have been measured at several temperatures. The values of the rates, krel, at 70° relative to that for [9-3H]phenanthrene are (X =) Me, 180; F, 4·1; Cl, 0·185; Br, 0·11; I, 0·14. Change of temperature has a large effect on the activating influence of the methyl group, the values of krel being ∼420, ∼350, and 230 at 0, 25, and 50°, respectively. The relatively large activation by fluorine, and the order of deactivation by the other halogens point to a contribution from resonance effects relative to those from inductive effects which is unusually high for ortho-substituents.
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