Ionic Dissociation. I. A Hückel Molecular-Orbital Treatment of the Dissociation of Carboxylic Acids and Several Azine Compounds
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概要
- 論文の詳細を見る
The relationship between the <I>pK<SUB>a</SUB></I> value and the change in the electronic energy, <I>Δ</I>E, in the course of the dissociation, and the electronic structure of various mono-carboxylic acids and several azine compounds are discussed on the basis of the calculation by Hückel methods for σ and π electron systems. The parallelism between the p<I>K<SUB>a</SUB></I> and the calculated <I>Δ</I>E of the acids is observed. The σ electron densities of the –COOH proton and the O<SUP>−</SUP> lone pair, which is constituted by the released electron on the dissociation, run parallel with the p<I>k<SUB>a</SUB></I>′s. The delocalizability of the lone pair for the electrophilic reaction, and that of the proton for the nucleophilic reaction, have a linear relationship with the p<I>k<SUB>a</SUB></I>′s. Similar relations are seen in several azine compounds. Therefore, it may be said that the protonation will take place by means of the electrophilic attack at the lone pair, and that the deprotonation occurs by means of the nucleophilic attack at the proton.
- 公益社団法人 日本化学会の論文
著者
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Kato Hiroshi
Department Of Applied Biological Chemistry Graduate School Of Agricultural And Life Sciences The Uni
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Yonezawa Teijiro
Department of Fuel Chemistry Faculty of Engineering Kyoto University
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Yamabe Hiroko
Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University
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