5775-33-7

Upstream product

• 777851-20-4 N-chloro-p-nitrobenzenesulfonamide 
• 109-89-7 diethylamine 
• 121-44-8 triethylamine 
• 71-43-2 benzene 
• 144-86-5 N-chloro-4-methylbenzenesulfonamide 

Downstream Products

• 102316-33-6 ethyl-imidophosphoric acid triphenyl ester 
• 109-89-7 diethylamine 
• 108-90-7 chlorobenzene 
• 660-68-4 diethyl amine hydrochloride 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 5326-47-6 2-amino-5-iodobenzoic acid 
• 3167-69-9 diethyl-amidophosphoric acid diethyl ester 
• 814-49-3 diethyl chlorophosphate 
• 5929-96-4 4-Diaethylamino-cis-crotononitril 
• 5931-58-8 4-Diaethylamino-trans-crotononitril 
• 649-15-0 N,N-diethyl-4-methylbenzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 144-86-5 N-chloro-4-methylbenzenesulfonamide 
• 91509-10-3 trans-1-chlorocyclohexan-2-ol diethylamidosulfate 

Relevant academic research and scientific papers

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-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.

Kinetics and mechanism of chlorine exchange between chloramine-T and secondary amines

The kinetics and mechanisms of chlorine transfer from chloramine-T (CAT) to several amines are second order and independent of p-toluenesulfonamide concentration; thus, the reaction does not involve disproportionation of CAT to dichloramine-T. From the profile of pH versus rate, the following mechanisms were proposed: (1) reaction of the ionized species of CAT with the ionized amine (ionic mechanism) and (2) reaction of the un-ionized species of CAT with the un-ionized amine (nonionic mechanism). The second-order, pH- independent rate constants calculated for the ionic and nonionic mechanisms were 1.6 and 5 x 106 M-1 s-1, respectively. Although these two mechanisms are kinetically indistinguishable, the rate constant for the nonionic mechanism is of the same order of magnitude as those calculated for similar chlorination reactions involving nonionizable chloramines, such as N- chlorosuccinimide, N-chloroquinuclidine, and N-chloro-N- methylbenzenesulfonamide. The proposed mechanism for the chlorine exchange involves a molecule of water in a cyclic, six-membered transition state.