Selective Electrochemical Reduction on the Imino Group of ${\alpha},{\beta}$-Dibenzyl N-Benzylidene L-Aspartate

${\alpha},{\beta}$-Dibenzyl N-Benzylidene L-Aspartate 의 Imino 기에 대한 선택적 전해환원반응

  • 김일광 (원광대학교 자연과학대학 화학과) ;
  • 김윤근 (원광대학교 자연과학대학 화학과) ;
  • 이영행 (원광대학교 자연과학대학 화학과) ;
  • 채규윤 (원광대학교 자연과학대학 화학과)
  • Published : 1989.12.20

Abstract

The electrochemical reduction of ${\alpha},{\beta}$-dibenzyl N-benzylidene L-aspartate in 0.1M LiCl ethanol solution was investigated by direct current (DC), differential pulse (DP) polarography, cyclic voltammetry and controlled potential coulometry(CPC). The irreversible reductive amination of imino group proceeded to form ${\alpha},{\beta}$-dibenyl N-benzyl L-aspartate by CEC or CE electrochemical reaction mechanism at the first reduction step (-0.92 volts vs. Ag-AgCl). The polarographic reduction wave was slightly suppressed due to inhibitory effect of micelle, while the irreversibility was increased according to the increase of Triton X-100 concentration. Upon the basis of product analysis and polarogram interpretation with pH change, possible CE electrode reaction mechanism was suggested.

0.1M LiCl의 ethanol 용액에서 ${\alpha},{\beta}$-dibenzyl N-benzylidene L-aspartate의 전기화학적 환원을 direct current, differential pulse polarography, cyclic voltammetry 그리고 controlled potential coulometry 방법으로 연구하였다. ${\alpha},{\beta}$-dibenzyl N-benzylidene L-aspartate의 환원과정은 1단계(-0.92 volts vs. Ag-AgCl)에서 양성자 첨가와 2전자이동에 의한 완전 비가역의 CEC 혹은 CE 반응기구로 진행되었으며 ${\alpha},{\beta}$-dibenzyl N-benzyl L-aspartate가 생성되었다. 계면활성제가 포함된 용액에서 polarography 환원파는 전체적으로 약간 억제되었으며 Triton X-100의 농도가 진해질수록 비가역성을 증가시키는 것으로 나타났다. 생성물 분석과 pH 변화에 따른 전극환원과정에 대한 고찰로 전기화학적 반응기구를 제안하였다.

Keywords

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