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Concerted mechanism of the aminolysis of 2,4,6-trinitrophenyl o-ethyl dithiocarbonate in aqueous ethanol

✍ Scribed by Enrique A. Castro; María Cubillos; Gabriel Muñoz; José G. Santos

Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
255 KB
Volume
26
Category
Article
ISSN
0538-8066

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✦ Synopsis

The reactions of the title substrate with a series of secondary alicyclic amines are subjected to a kinetic study in 44 wt% aqueous ethanol, 25.0°C, and ionic strength 0.2 M (KC1). The Bronsted-type plot (log k~ vs. pKa of the amine, where k~ is the second-order rate coefficient) obtained is linear with slope p = 0.53, which indicates a concerted mechanism. The predicted Bronsted break for a hypothetical stepwise mechanism is pK,O = 8.7, which was not observed (pKa range of amines: 6-11). The same reaction in water is stepwise, which shows that the tetrahedral intermediate found in water is much destabilized by the change of solvent from water to aqueous ethanol.

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