Kinetics and mechanism of the oxidation of some hexoses by sodium n-chlorobenzenesulfonamide in the presence of sodium-hydroxide

The kinetics of the oxidation of d-glucose, d-mannose, d-galactose and d-fructose by sodium N-chlorobenzenesulphonamide or Chloramine-B (CAB) in the presence of alkali at 35° has been investigated, and the rate = k[CAB][hexose][HO−] was observed. The product, benzensulphonamide, had no influence, increase of ionic strength increased the rate, and the rate decreased when the dielectric constant of the medium was decreased. The proton inventory was studied for the reactions in H2OD2O mixtures. The rates increased in the order d-fructose >d-galactose >d-glucose >d-mannose. An isokinetic relation was observed with β 347 K, which showed the reaction to be enthalpy-controlled