Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Mechanism of the Solvent Effect in a Binary Solvent System on the Cationic Polymerization of N-Phenylethylenimine
Tsutomu KagiyaTomizo Kondo
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1969 Volume 42 Issue 12 Pages 3514-3518


The effect of the binary solvent systems on the polymerization of N-phenylethylenimine with a formic acid catalyst was studied quantitatively. In an acetonitrile-acetone system composed of components with similar nucleophilicities but with very different dielectric constants, the polymerization rate increases with an increase in the dielectric constant of the binary solvent system. In an acetonitrile - N,N-dimethylacetamide system composed of components with very different nucleophilicities but with similar dielectric constants, on the other hand, the rate was markedly depressed by the addition of a small amount of N,N-dimethylacetamide with a large nucleophilicity. On the basis of these results, a mechanism of the solvent effect in a binary solvent system was proposed; the rate equation of the polymerization was expressed empirically as a function of both the dielectric constant of the binary solvent mixture and the nucleophilic equilibrium constant, and the concentration of the component.

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