Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Electrochemical Reduction on the -S-N= Bond of N-Oxyldiethylenebenzothiazole-2-sulfenamide

N-Oxyldiethylenebenzothiazole-2-sulfenamide의 -S-N= 결합에 대한 전기화학적 환원

  • Kim, Hae-Jin (Department of Chemistry, Chonnam National University) ;
  • Jung , Keun-Ho (Department of Chemical Education, Chonnam National University) ;
  • Choi, Qw-Won (Department of Chemistry, Seoul National University) ;
  • Kim, Il-Kwang (Department of Chemistry, Wonkwang University) ;
  • Leem, Sun-Young (Department of Chemistry, Chonnam National University)
  • 김해진 (전남대학교 자연대학 화학과) ;
  • 정근호 (전남대학교 사범대학 화학교육과) ;
  • 최규원 (서울대학교 자연대학 화학과) ;
  • 김일광 (원광대학교 자연대학 화학과) ;
  • 임선영 (전남대학교 자연대학 화학과)
  • Published : 19911100
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Abstract

The electrochemical reduction of N-oxyldiethylenebenzothiazole-2-sulfenamide (ODBS; vulcanization accelerator) was investigated by direct current polarography, differential pulse polarography, cyclic voltammetry and controlled potential coulometry. The irreversible electrode reduction of ODBS proceeded E-C-E-C reaction mechanism by three electrons transfer with irreversible one wave (-1.86 volts vs. Ag/0.1 M AgN$O_3$ in AN). As the results of controlled potential electrolysis, mercaptobenzothiazole (MBT), benzothiazole disulfide (MBT dimer) and extricated sulfur were products which followed by cleavage of the sulfenamide (-S-N=) bond. Upo the basis of products analysis and polarogram interpretation witli pH variable, electrochemical reaction mechanism was suggested.

N-Oxyldiethylenebenzothiazole-2-sulfenamide (ODBS;가황산촉진제)의 전기화학적 환원을 직류와 시차펄스 폴라로그래피 순환 전압전류법, 조절전위 전기량법으로 연구하였다. ODBS의 전극환원과정은 단일 환원파(-1.86 volts vs. Ag/0.1 M AgN$O_3$in AN)에서 비가역으로 3전자가 이동하는 E-C-E-C 반응 메카니즘으로 진행되었다. 조절전위 전기분해 결과 SULFENAMIDE(-S-N=) 결합이 끊어지고 mercaptobenzothiazole(MBT)과 benzothiazole disulfide(MBT dimer) 그리고 유리된 sulfur 등이 생성물로 얻어졌따. pH 변화에 따른 폴라로그램의 해석과 생성물 분석의 결과를 바탕으로하여 전기화학적 반응 메카니즘을 제안하였다.

Keywords

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