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Kinetics and mechanism of the reaction of N ‐chlorosuccinimide with I − and OH −
Author(s) -
Agulla B.,
Antelo J. M.,
Arce F.,
Parajó M.
Publication year - 2005
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.20073
Subject(s) - chemistry , iodide , catalysis , ion , reaction mechanism , hydroxide , inorganic chemistry , order of reaction , kinetics , proton , base (topology) , chemical kinetics , aqueous solution , medicinal chemistry , reaction rate constant , organic chemistry , mathematical analysis , physics , mathematics , quantum mechanics
In this kinetic study of the reaction between the iodide ion and the N ‐chlorosuccinimide, 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. © 2005 Wiley Periodicals, Inc. Int J Chem Kinet 37: 243–252, 2005