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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 15, Number 7
BKCSDE 15(7)
July 20, 1994 

The Effects of Solvation and Polarizability on the Reaction of S-p-Nitrophenyl Thiobenzoate with Various Anionic Nucleophiles
Ik-Hwan Um*, Ga-Ryung Kim, Dong-Sook Kwon
Second-order rate constants have been measured spectrophotometrically for the nucleophilic substitution reactions of S-p-nitrophenyl thiobenzoate with various anionic nucleophiles including 6 α-effect nucleophiles. A good Brφ nsted 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 Brφnsted plot. The deviations are attributed to the effect of polarizability and solvation rather than a change in the reaction mechanism. The α-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 α-effect.
585 - 589
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