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The Effects of Solvation and Polarizability on the Reaction of S-p-Nitrophenyl Thiobenzoate with Various Anionic Nucleophiles
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  • The Effects of Solvation and Polarizability on the Reaction of S-p-Nitrophenyl Thiobenzoate with Various Anionic Nucleophiles
  • The Effects of Solvation and Polarizability on the Reaction of S-p-Nitrophenyl Thiobenzoate with Various Anionic Nucleophiles
저자명
Um. Ik-Hwan,Kim. Ga-Ryung,Kwon. Dong-Sook
간행물명
Bulletin of the Korean Chemical Society
권/호정보
1994년|15권 7호|pp.585-589 (5 pages)
발행정보
대한화학회
파일정보
정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

Second-order rate constants have been measured spectrophotometrically for the nucleophilic substitution reactions of S-p-nitrophenyl thiobenzoate with various anionic nucleophiles including 6 ${alpha}$-effect nucleophiles. A good Bronsted correlation has been observed for the reactions with 7 aryloxides. However, p-chlorothiophenoxide and hydroxide ions exhibit significantly positive and negative deviations, respectively, from the Bronsted plot. The deviations are attributed to the effect of polarizability and solvation rather than a change in the reaction mechanism. The ${alpha}$-effect nuceophiles except highly basic ones demonstrate remarkably enhanced nucleophilicity. The effects of solvation and/or polarizability are proposed to be important for the cause of the ${alpha}$-effect.