Charge-transfer Interaction and Chemical Reaction. IV. Reactions of <I>para</I>-Substituted Derivatives of Aniline with Chloranil
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概要
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Interactions of chloranil with <I>p</I>-phenyIenediamine, <I>N</I>,<I>N</I>-dimethyl-<I>p</I>-phenyIenediamine, and <I>N</I>,<I>N</I>,<I>N</I>′,<I>N</I>′-tetramethyl-<I>p</I>-phenylenediamine were studied by measuring visible and ultraviolet absorption spectra at various temperatures between 77°K and 300°K. In an ether-isopropyl alcohol (3:1) mixed solvent, the <I>p</I>-phenylenediamine- and <I>N</I>,<I>N</I>-dimethyl-<I>p</I>-phenylenediamine-chloranil systems were led to the substitution reaction through the outer complex and the ionic species as reaction intermediates. In ethyl ether, the <I>p</I>-phenylenediamine- and <I>N</I>,<I>N</I>-dimethyl-<I>p</I>-phenylenediamine-chloranil systems were found to yield the inner complex and the substituted species through the outer complex, respectively. In the <I>N</I>,<I>N</I>,<I>N</I>′,<I>N</I>′-tetramethyl-<I>p</I>-phenylenediamine-chloranil system, the inner complex was found to be formed <I>via</I> a clustering of the outer complexes.<BR>The interactions between aromatic amines and chloranil were found to be classified into the following three types: (a) the charge-transfer (outer or inner) complex is formed between an electron donor and an acceptor and no further reaction proceeds; (b) the substitution reaction occurs through the outer and inner complexes; (c) the substitution reaction occurs through the outer complex and ionic species. The difference in the reactivities between mtfta-substituted derivatives of aniline and <I>ortho</I>- and <I>para</I>-substituted ones was explained by taking the π-electron density on the amino group into account.
- 公益社団法人 日本化学会の論文
著者
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Nagakura Saburo
The Institute for Solid State Physics The University of Tokyo
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Yoshihara Keitaro
The Institute for Solid State Physics, The University of Tokyo
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Nogami Takashi
The Institute for Solid State Physics, The University of Tokyo
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Nagakura Saburo
The Institute for Molecular Science
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