Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Micellar Catalysis on the Hydrolysis of the Fungicidal N-[1-(benzotriazol-1-yl)benzyl]aniline

항균성, N-[1-(benzotriazol-1-yl)benzyl]aniline의 가수분해 반응에 미치는 미셀 촉매효과

  • Sung, N.D. (Department of Agricultural Chemistry, Chungnam National University) ;
  • Park, C.K. (Department of Agricultural Chemistry, Chungnam National University) ;
  • Lim, C.W. (Department of Agricultural Chemistry, Chungnam National University)
  • 성낙도 (충남대학교 농과대학 농화학과) ;
  • 박천규 (충남대학교 농과대학 농화학과) ;
  • 임치환 (충남대학교 농과대학 농화학과)
  • Published : 1994.06.30
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Abstract

The hydrolysis of fungicidal N-[1-(benzotriazol-1-yl)benzyl]aniline (BBA) molecule in the presence of cationic cetyltrimethylammonium bromide (CTABr) and anionic sodium laurylsulfate (NaLs) micellar solutions has been studied kinetically. The Micellar catalysis effect shows that the rate is slightly accelerated by the addition of the anionic NaLs at high pH and the binding constant (Ks) is $1.45{\times}10^4M^{-1}$. This result presumably is due to the electrostatic stabilization by the anionic micelle of the developing carbocation in the transition state rather than the hydrophobic character (${\pi}$: 4.93) of (BBA).

이온성 계면활성제인 sodium laurylsulfate(NaLs)와 cetyltrimethylammonium bromide(CTABr)의 존재하에서 항균성 N-[1-(benzotriazol-1-yl)benzyl]aniline(BBA)분자의 가수 분해 반응에 미치는 미셀효과를 검토한 바, NaLs가 존재하는 높은 pH에서 미셀 촉매효과가 나타났으며 결합상수(Ks)는 $1.45{\times}10^4M^{-1}$이었다. 이와 같은 미셀 촉매효과는 (BBA)의 소수성(${\pi}$: 4.93)보다 전이상태에서 생성되는 carbocation이 음이온성 미셀에 의한 정전기적 안정화에 기인한 결과로 보여진다.

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