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Kinetic study of the formation of N‐chloro compounds using N‐chlorosuccinimide
Authors:Cristina Pastoriza  Juan Manuel Antelo  Juan Crugeiras  Angeles Peña‐Gallego
Institution:1. Departamento de Química Física, Facultad de Química, Universidad de Santiago de Compostela, , 15782 La Coru?a, Spain;2. Departamento de Química Física, Facultad de Química, Universidad de Vigo, , 36310 Vigo, Spain
Abstract:Second‐order rate constants were determined for the chlorination reaction of 2,2,2‐trifluoethylamine and benzylamine with N‐chlorosuccinimide at 25 °C and an ionic strength of 0.5 M. These reactions were found to be of first order in both reagents. According to the experimental results, a mechanism reaction was proposed in which a chlorine atom is transferred between both nitrogenous compounds. Kinetics studies demonstrate that the hydrolysis process of the chlorinating agent does not interfere in the chlorination process, under the experimental conditions used in the present work. Free‐energy relationships were established using the results obtained in the present work and others available in the literature for chlorination reactions with N‐chlorosuccinimide, being the pKa range included between 5.7 and 11.22. Copyright © 2014 John Wiley & Sons, Ltd.
Keywords:free relationships  kinetics and mechanism  N‐chloramines  N‐chlorination  N‐chlorosuccinimide
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