Hydrolysis Mechanism of N-(benzenesulfonyl)-C-(N-methylanilino)imidoyl Chloride Derivatives

N-(benzenesulfonyl)-C-(N-methylanilino)imidoyl Chloride 유도체의 가수분해 반응 메카니즘

  • Kwon, Ki-Sung (Department of Chemistry, Chungnam National University) ;
  • Song, Yun-Yi (Department of Chemistry, Chungnam National University)
  • 권기성 (충남대학교 자연과학대학 화학과) ;
  • 송윤이 (충남대학교 자연과학대학 화학과)
  • Published : 19950800


Rate Constants of hydrolysis of N-(benzenesulfonyl)-C-(N-methylanilino)imidoyl chlorides were determined by UV spectrophotometry in 50% (v/v) aqueous methanol at 25$^{\circ}C.$ On the basis of rate equation, substituent effect, solvent effect, salt effect, thermodynamic parameters and hydrolysis product analysis, it may be concluded that the hydrolysis of N-(benzenesulfonyl)-C-(N-methylanilino)imidoyl chlorides proceed through $S_N1$ mechanism via azocarbonium ion intermediate below pH 9.0, while aebove pH 10.0 the hydrolysis proceeds through nucleophilic addition-elimination ($Ad_{N-E}$) mechanism.



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