A study of the reduction mechanism of p-dimethylaminobenzaldehyde to 1,2-bis(p-dimethylaminophenyl)-1,2-ethanediol by rotating disk electrode voltammetry.
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概要
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Rotating disk electrode voltammetry was applied to study the reduction mechanism of <I>p</I>-dimethylaminobenzaldehyde (<B>1</B>) in water–ethanol alkaline solutions by using a mercury-plated platinum rotating disk electrode. In the logarithmic analysis of the wave, the plots of log [<I>i</I><SUP>2⁄3</SUP>/(<I>i</I><SUB>d</SUB>–<I>i</I>)] <I>vs.</I> <I>E</I> showed good linearity, and the shifts of the half-wave potential with an increase in the rotation speed of the electrode (ω) and in the initial concentration of <B>1</B> (<I>C</I>) were ∂<I>E</I><SUB>1⁄2</SUB>⁄∂logω=−22±2 mV and ∂<I>E</I><SUB>1⁄2</SUB>⁄∂log<I>C</I>=19±2 mV, respectively. On the other hand, no appreciable change in <I>E</I><SUB>1⁄2</SUB> was observed with varying alkalinities of the solutions. These results and the large shift of <I>E</I><SUB>1⁄2</SUB> with an increase in the concentration of water (∂<I>E</I><SUB>1⁄2</SUB>⁄∂log[H<SUB>2</SUB>O]=<I>ca.</I> 50 mV) are explained in terms of the following reactions:<BR>R+e\rightleftarrowsR<SUP>\newdot</SUP> (solvated by water), (1)<BR>2R<SUP>\newdot</SUP>\overset<I>k</I>→D<SUP>2−</SUP> (r.d.s.), (2)<BR>D<SUP>2−</SUP>+2H<SUB>2</SUB>O→DH<SUB>2</SUB>+2OH<SUP>−</SUP>, (3)<BR>where R and R<SUP>\newdot</SUP> are the molecule and the radical of <B>1</B>, respectively, D<SUP>2−</SUP> is the dimer of R<SUP>\newdot</SUP> and DH<SUB>2</SUB> is the hydro-dimer (<B>2</B>) of R. The rate of the dimerization reaction (<I>k</I> in Eq. 2) was estimated to be 2.5×10<SUP>4</SUP> M<SUP>−1</SUP> s<SUP>−1</SUP> from the shift of <I>E</I><SUB>1⁄2</SUB> with logω for the 50% water-ethanol solution containing 1 M NaOH, and this rate constant decreased with decreasing water concentration.
- 公益社団法人 日本化学会の論文
著者
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Taniguchi Isao
Department Of Applied Chemistry & Biochemistry Faculty Of Engineering Kumamoto University
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Yoshiyama Akiko
Department Of Electric Chemistry Tokyo Institute Of Technology
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Yasukouchi Kazuo
Department of Industrial Chemistry, Faculty of Engineering, Kumamoto University
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SEKINE TARO
Department of Chemical Engineering, Niigata University
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