Platinum(II)-Olefin Complexes Containing Amino Acids. III. Optical Inversion and Substitution of Coordinated Olefins in Optically Active <I>trans</I>(<I>N</I>)-Chloro-L-prolinato-olefinplatinum(II) Complexes in Organic Solvents

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概要

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• Optical inversion of coordinated 2-methyl-2-butene and <I>trans</I>-2-butene in <I>trans</I>(<I>N</I>)-chloro-L-prolinato-olefinplatinum(II), <I>trans</I>(<I>N</I>)-[PtCl(L-prol)(olefin)] (nitrogen of L-prolinate ion is <I>trans</I> to the olefin), <I>i.e.</I> the interconversion between diastereoisomers (Fig. 1), has been kinetically studied in acetone by measuring the decrease in the intensity of circular dichroism (CD) in near ultraviolet region. The rate was measurable only in the presence of olefin, and can be expressed by the relation, Rate=<I>k</I>[complex][olefin]. The <I>E<SUB>a</SUB></I> and the <I>ΔS</I><SUP>\neweq</SUP> values for the two complexes are 7.8±1.0 and 9.0±1.0 kcal/mol, and −44 and −39 entropy unit, respectively. The coordinated <I>trans</I>-2-butene is replaced by other olefins, 2,3-dimethyl-2-butene, 2-methyl-2-butene, <I>trans</I>-2-butene (optical inversion), and styrene, under similar conditions to give the same rate formula. The second order rate constant increases in the given order. The inversion seems to take place <I>via</I> bimolecular mechanism with excessive olefin as nucleophile. The corresponding complexes containing styrene and its <I>para</I> derivatives give such an inversion much faster in the absence of excess of olefin. With change of <I>para</I> substituents, the rate increases in the order, methoxy<methyl<hydrogen<chloro<nitro. This seems to be related with their electrondrawing ability.

• 公益社団法人 日本化学会の論文

著者

• Saito Kazuo

  Department Chemistry Faculty Of Science Tohoku University

• Fujita Junnosuke

  Department of Chemistry Faculty of Science Osaka University

• KIDO Hiroaki

  Department of Chemistry, College of Engineering, Nihon University

• Konya Kazuo

  Department of Chemistry, Faculty of Science, Tohoku University

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• タイトル無し
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