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• W2006653652 abstract "Abstract The reactions of pyridines and secondary alicyclic (SA) amines with phenyl and 4‐nitrophenyl chlorodithioformates (PClDTF and NPClDTF, respectively) are subjected to a kinetic study in aqueous ethanol (44 wt% ethanol) solution, at 25.0 °C, and an ionic strength of 0.2 M (KCl). The reactions are studied spectrophotometrically. Under amine excess, pseudo‐first‐order rate coefficients ( k obs ) are found. Plots of k obs versus [amine] are linear and pH independent, with slope k N . The Brønsted‐type plots (log k N vs . p K a of aminium ions) are linear for the reactions of PClDTF with SA amines (slope β of 0.3) and pyridines ( β = 0.26) and those of NPClDTF with pyridines ( β = 0.30). For the reaction of NPClDTF with SA amines the Brønsted‐type plot is biphasic, with slopes β 1 = 0.2 (at high p K a) and β 2 = 1.1 (at low p K a). The p K a value at the center of curvature (p K ) is 7.7. The magnitude of the slopes indicates that the mechanisms of these reactions are stepwise, with the formation of a zwitterionic tetrahedral intermediate as the rate‐determining step, except for the reaction of NPClDTF with SA amines where there is a change in the rate‐determining step, from formation to breakdown of the tetrahedral intermediate, as the amine basicity decreases. Copyright © 2009 John Wiley & Sons, Ltd." @default.
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• W2006653652 date "2009-04-28" @default.
• W2006653652 modified "2023-10-09" @default.
• W2006653652 title "Kinetics and mechanism of the reactions of aryl chlorodithioformates with pyridines and secondary alicyclic amines" @default.
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• W2006653652 doi "https://doi.org/10.1002/poc.1555" @default.
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