Kinetic study of the formation of N‐chloro compounds using N‐chlorosuccinimide. (20th January 2014)

• Record Type: Journal Article
• Authors: Pastoriza, Cristina; Antelo, Juan Manuel; Crugeiras, Juan; Peña‐Gallego, Angeles
• Is Part Of: Journal of physical organic chemistry. Volume 27:Number 5(2014:May)
• Page Start: 407
• Page End: 418
• Publication Date: 2014-01-20
• Subjects: Chemistry, Physical organic -- Periodicals; 547.1
• DOI: 10.1002/poc.3278
• Languages: English
• ISSNs: 0894-3230

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Second‐order rate constants were determined for the <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">chlorination</named-content> reaction of 2, 2, 2‐trifluoethylamine and benzylamine with <italic>N</italic>‐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 <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">hydrolysis</named-content> process of the chlorinating agent does not interfere in the <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">chlorination</named-content> 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 <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">chlorination reactions</named-content> with <italic>N</italic>‐chlorosuccinimide, being the p<italic>K</italic><sub>a</sub> range included between 5.7 and 11.22. Copyright © 2014 John Wiley & Sons, Ltd.</p> </abstract>