Structure—Activity Considerations in Kinetics and Mechanism of Chlorine Exchange Between Chloramine‐T and Secondary Amines

To study the mechanism of N-chlorination of secondary amines by chloramine‐T, the kinetics of the reactions of some aromatic-substituted analogues of N-chlorobenzenesulfonamide with various secondary amines were determined. The importance of amine basicity and reactivity of the N–Cl bond of the N-ch...

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Bibliographic Details
Published in:Journal of pharmaceutical sciences 1992-07, Vol.81 (7), p.657-660
Main Authors: Dannan, Hana, Hussain, Anwar, Crooks, Peter A., Dittert, Lewis W.
Format: Article
Language:English
Subjects:
Algorithms
Amines - chemistry
Anti-Infective Agents, Local - pharmacology
Biological and medical sciences
Chloramines - pharmacology
Chlorine - chemistry
Disinfectants - pharmacology
Drug toxicity and drugs side effects treatment
Hydrogen-Ion Concentration
In Vitro Techniques
Indicators and Reagents - pharmacology
Kinetics
Medical sciences
Miscellaneous (drug allergy, mutagens, teratogens...)
Pharmacology. Drug treatments
Structure-Activity Relationship
Tosyl Compounds
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Summary:To study the mechanism of N-chlorination of secondary amines by chloramine‐T, the kinetics of the reactions of some aromatic-substituted analogues of N-chlorobenzenesulfonamide with various secondary amines were determined. The importance of amine basicity and reactivity of the N–Cl bond of the N-chlorobenzenesulfonamide was also assessed. The results indicate that a mechanism involving the un-ionized species of both reactants (i.e., a molecular mechanism), rather than an ionic mechanism, is operating and that the reaction most likely proceeds via a six-membered-ring transition state that incorporates a water molecule.
ISSN:0022-3549
1520-6017
DOI:10.1002/jps.2600810713