TY - JOUR
T1 - Electrochemical Study of the SN2 Reaction of 1-p-Toluenesulfonyl-2,4-dinitronaphthalene with Hydroxide Ions at the Nitrobenzene-Water Interface
AU - Kong, Young Tae
AU - Imabayashi, Shin Ichiro
AU - Kakiuchi, Takashi
PY - 1998
Y1 - 1998
N2 - The rate of the interfacial nucleophilic reaction of 1-p-toluenesulfonyl-2,4-dinitronaphthalene (TSDNN) with OH- ions at the polarized nitrobenzene (NB)-water (W) interface was studied using a polarographic technique. The TSDNN partitioned into the aqueous phase underwent a displacement of the p-toluenesulfonyl moiety with OH-. The transfer of one of the products, 2,4-dinitronaphthalate (DNN-), from the W phase to the NB phase was monitored as the current across the interface. The rate constant of the reaction of TSDNN with OH- in the aqueous phase was estimated to be 1.03±0.23 dm3 mol-1 s-1 at 25°C, which is ten-times higher than the rate constant of the displacement of 2,4-dinitrofluorobenzene with OH- in the aqueous phase, 1.01±0.13×10-1 dm3mol-1 s-1. The contribution from the reactions in the NB phase and at the interface to the formation of DNN- seems to be negligible, suggesting the absence of an interfacial facilitation of the reaction.
AB - The rate of the interfacial nucleophilic reaction of 1-p-toluenesulfonyl-2,4-dinitronaphthalene (TSDNN) with OH- ions at the polarized nitrobenzene (NB)-water (W) interface was studied using a polarographic technique. The TSDNN partitioned into the aqueous phase underwent a displacement of the p-toluenesulfonyl moiety with OH-. The transfer of one of the products, 2,4-dinitronaphthalate (DNN-), from the W phase to the NB phase was monitored as the current across the interface. The rate constant of the reaction of TSDNN with OH- in the aqueous phase was estimated to be 1.03±0.23 dm3 mol-1 s-1 at 25°C, which is ten-times higher than the rate constant of the displacement of 2,4-dinitrofluorobenzene with OH- in the aqueous phase, 1.01±0.13×10-1 dm3mol-1 s-1. The contribution from the reactions in the NB phase and at the interface to the formation of DNN- seems to be negligible, suggesting the absence of an interfacial facilitation of the reaction.
KW - 1-p-toluenesulfonyl-2,4-dinitronaphthalene
KW - Nucleophilic substitution reaction
KW - Polarized nitrobenzene-water interface
KW - Polarography
KW - S2 reaction
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U2 - 10.2116/analsci.14.121
DO - 10.2116/analsci.14.121
M3 - Article
AN - SCOPUS:0032397751
VL - 14
SP - 121
EP - 125
JO - Analytical Sciences
JF - Analytical Sciences
SN - 0910-6340
IS - 1
ER -