Kinetics and mechanism of the reaction of N‐chlorosuccinimide with I⁻ and OH⁻

Abstract

In this kinetic study of the reaction between the iodide ion and the Nchlorosuccinimide, we have found that the reaction is first order in N-chlorosuccinimide: namely, first order with respect to the iodide ion and first order with respect to the proton concentration. Based on the experimental results, we propose a mechanism consistent in Cl + transfer from the N-chlorosuccinimide to the iodide ion. We have found that the reaction presents general acid catalysis with a Brönsted exponent value of 0.10. In addition, given that the N-chlorocompounds are not stable in aqueous solution, we have carried out a study on the influence of bases in the presence of N-chlorosuccinimide. We have found that the reaction is first order in hydroxide ion, as well as in the 1,1,1,3,3,3-hexafluoroisopropanoxide ion and the 2,2,2-trifluorethoxide ion, which shows that the reaction is general-base catalyzed. C 2005 Wiley Periodicals, Inc. Int J Chem Kinet 37: [243][244][245][246][247][248][249][250][251][252] 2005

Mechanism of Oxidation of (p‐Substituted Phenylthio)acetic Acids with N‐Bromophthalimide

“…The diverse nature of the chemistry of these compounds is due to their ability to act as sources of halonium cations, hypohalite species and nitrogen anions, which act both as bases and nucleophiles 3 . A review of literature shows that N-halo compounds such as N-halo-succinimides [4][5][6][7] , N-halosulphonamides [8][9][10][11] (chloramine-T, bromamine-T, chloramine-B, bromamine-B, etc. ), N-haloamides [12][13][14] (N-haloacetamides, N-bromobenzamide, N-chloronicotinamide, etc.…”