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Kinetics and mechanism of the reactions of O-aryl S-(4-nitrophenyl) dithiocarbonates with anilines in aqueous ethanol by Enrique A. Castro; Marcela Gazitúa; José G. Santos is a Chemistry article available to read on EtoBox.

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## Abstract The reactions of __O__‐(4‐methylphenyl) __S__‐(4‐nitrophenyl) dithiocarbonate and __O__‐(4‐chlorophenyl) __S__‐(4‐nitrophenyl) dithiocarbonate with a series of anilines are subjected to a kinetic investigation in 44 wt% ethanol–water, at 25.0 °C and an ionic strength of 0.2 M. The reactions are followed spectrophotometrically at 420 nm (appearance of 4‐nitrobenzenethiolate anion). Under excess amine, pseudo‐first‐order rate coefficients (__k__~obs~) are found. For the reactions of both substrates with anilines, plots of __k__~obs~ __versus__ free amine concentration at constant pH are nonlinear upwards, according to a second‐order polynomial equation. This kinetic behavior is in agreement with a stepwise mechanism consisting of two tetrahedral intermediates, one zwitterionic (T^±^) and the other anionic (T^−^), with a kinetically significant proton transfer from T^±^ to an aniline to yield T^−^. The rate equation was derived from the proposed mechanism. By nonlinear least‐squares fitting of the rate equation to the experimental data, values of the rate micro‐coefficients involved in both steps were determined. Copyright © 2009 John Wiley & Sons, Ltd.

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Author

Enrique A. Castro; Marcela Gazitúa; José G. Santos

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Inc.; Wiley (ISSN 0894-3230)

Published

2009

Language

EN

Field

Chemistry (Physical Sciences)