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Reactions of chlorination with tert ‐butyl hypochlorite ( T BuOCl)
Author(s) -
Pastoriza Cristina,
Antelo Juan Manuel,
Crugeiras Juan
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.3377
Subject(s) - chemistry , hypochlorite , medicinal chemistry , organic chemistry
The chlorination reactions of nitrogenous organic compounds (2,2,2‐trifluoroethylamine, benzylamine, glycine, and dimethylamine) by tert ‐butyl hypochlorite ( t BuOCl) were studied at 25 °C, ionic strength 0.5 M and under isolation conditions. The kinetic results obtained in the formation processes of the corresponding N ‐chloramines in acid medium (pH = 5–7) are summarized in this paper. Kinetic studies showed a first order with respect to t BuOCl concentration. The chlorination reactions involving benzylamine, glycine and dimethylamine were all first order with respect to nitrogenous compound concentration and approximately −1 order with respect to proton concentration. The reaction with 2,2,2‐trifluoroethylamine was more complex, and the order of reaction with respect to the amine varied with pH. Copyright © 2014 John Wiley & Sons, Ltd.