Abstract
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.
Original language | English |
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Pages (from-to) | 121-125 |
Number of pages | 5 |
Journal | Analytical Sciences |
Volume | 14 |
Issue number | 1 |
DOIs | |
Publication status | Published - 1998 |
Externally published | Yes |
Keywords
- 1-p-toluenesulfonyl-2,4-dinitronaphthalene
- Nucleophilic substitution reaction
- Polarized nitrobenzene-water interface
- Polarography
- S2 reaction
ASJC Scopus subject areas
- Analytical Chemistry