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Influence of Substituent Groups on Nuclear Reactivity in the Formation of Substituted Biphenyls by Reaction of Aromatic Diazo and Related Compounds with Aromatic Liquids. VII. <I>p</I>-Nitrophenylation and <I>p</I>-Methoxyphenylation
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- Itô Ryôichi
- Department of Chemistry Faculty of Science The University of Tokyo
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- Migita Toshihiko
- Department of Chemistry Faculty of Science The University of Tokyo
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- Morikawa Naotake
- Department of Chemistry Faculty of Science The University of Tokyo
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- Okuni Morihiko
- Department of Chemistry Faculty of Science The University of Tokyo
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- Simamura Osamu
- Department of Chemistry Faculty of Science The University of Tokyo
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Description
N-Nitroso-p-nitroacet(anilide-14C) and N-nitroso-p-methoxyacet(anilide-14C) have been decomposed at 20.0°C in mixtures of benzene and monosubstituted benzenes C6H5X (X=NO2, Cl, OCH3, and CH3), and the reaction products have been analyzed for 4-nitro-and 4-methoxybiphenyl and isomeric 4-NO2C6H4C6H4X and 4-CH3OC6H4C6H4X by the isotope dilution method.<BR>From the results of these competitive experiments, the partial rate factors for the p-nitrophenylation and p-methoxyphenylation have been calculated (Tables I and II).<BR>The values of the partial rate factor for the meta position give a satisfactory Hammett plot with a slope of −0.81 for the p-nitrophenylation and one with a slope of +0.09 for the p-methoxyphenylation, showing that the p-nitrophenyl radical has a pronounced electrophilic character while the p-methoxyphenyl radical has little, if any, nucleophilic character.
Journal
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 36 (8), 985-991, 1963
The Chemical Society of Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390282679108118144
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- NII Article ID
- 130001961886
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- ISSN
- 13480634
- 00092673
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- Text Lang
- en
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- Data Source
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- JaLC
- Crossref
- CiNii Articles
- OpenAIRE
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- Abstract License Flag
- Disallowed