Premium
Kinetic study of the formation of N ‐chloro compounds using N ‐chlorosuccinimide
Author(s) -
Pastoriza Cristina,
Antelo Juan Manuel,
Crugeiras Juan,
PeñaGallego Angeles
Publication year - 2014
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3278
Subject(s) - chemistry , chlorine , reagent , hydrolysis , chlorine atom , ionic strength , kinetics , benzylamine , reaction rate constant , reactivity (psychology) , medicinal chemistry , kinetic energy , activation energy , computational chemistry , organic chemistry , aqueous solution , medicine , physics , alternative medicine , pathology , quantum mechanics
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 p K a range included between 5.7 and 11.22. Copyright © 2014 John Wiley & Sons, Ltd.