Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Electrochemical Behaviors of N'-phenyl-N-(2-chloroethyl)-N-nitrosourea Analogous and Synthesis of N-aminourea

N'-phenyl-N-(2-chloroethyl)-N-nitrosourea 유사체의 전기화학적 거동 및 N-aminourea의 합성

  • Won, Mi-Sook (Department of Chemistry, Pusan National University) ;
  • Kim, Jeong-Gyun (Department of Chemistry, Pusan National University) ;
  • Sim, Yoon-Bo (Department of Chemistry, Pusan National University)
  • 원미숙 (부산대학교 자연과학대학 화학과) ;
  • 김정균 (부산대학교 자연과학대학 화학과) ;
  • 심윤보 (부산대학교 자연과학대학 화학과)
  • Published : 19911100
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Abstract

N'-phenyl-N-(2-chloroethyl)-N-aminourea has been prepared from N'-phenyl-N-(2-chloroethyl)-N-nitrosourea by means of the electrochemical reduction with the mercury pool electrolytic cell. In order to find out the optimum condition of the reaction, the voltammetric behaviors for N'-aryl-N-(2-chloroethyl)-N-nitrosourea derivatives have been investigated by the cyclic voltammetry and polarography. The peak potentials was shifted to the negative direction as the pH value of the solution decrease. The substituent effects of phenyl ring on the peak potential were not observed in this case. (5:3) EtOH/4 N-HCl mixed solution was employed for the electrolysis. The applied potential was -0.7 V vs. Ag/AgCl/4 N-HCl electrode. The number of electrons participated to the reduction process was 4, respectively. The product was identified by FT-IR, NMR, mass and/or elemental analysis data.

수은 pool 전해조를 사용하여 (5:3) EtOH/4N-HCl 용액계에서 선택적인 -N-N=O기의 전기화학적 환원에 의해 N'-phenyl-N-(2-chloroethyl)-N-nitrosourea로부터 N'-phenyl-N-(2-chloroethyl)-N-aminourea를 합성하였다. 전기화학적 환원에 앞서 반응의 최적조건을 검토하기 위하여 몇 가지 N'-aryl-N-(2-chloroethyl)-N-nitrosourea 유사체에 대하여 pH변화에 따른 환원전위를 순환전압전류법으로 조사한 결과 pH에 따라 $E_p$값이 "-"쪽으로 이동하였으며 aryl기의 치환기 효과는 -N-N=O기의 환원 전위에 크게 영향을 미치지 않는 것으로 나타났다. 용액계의 pH에 따른 반응성을 조사한 결과 강산성 용액(pH<1)에서 반응이 가장 잘 진행되며 -0.7 V vs. Ag/AgCl/4 N-HCl에서 N-N=O기의 선택적인 4전자 환원반응에 의해 N-N$H_2$가 생성됨을 확인하였다.

Keywords

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