Reactivities of hypochlorous and hypobromous acid, chlorine monoxide, hypobromous acidium ion, chlorine, bromine, and bromine chloride in electrophilic aromatic substitution reactions with p-xylene in water

Bromination of aromatic compounds by residual bromide in sodium chloride matrix modifier salt during heated headspace GC/MS analysis

“…A mechanism for the bromination of aromatic compounds under the conditions reported here is supported by previous research involving treatment of aqueous systems containing Cl À , Br À , and H 2 O 2 , under acidic conditions [13][14][15] (Table 1; R5-R9). When acid is present, Cl À from sodium chloride is protonated to form hydrochloric acid.…”

Reactivity of BrCl, Br2, BrOCl, Br2O, and HOBr Toward Dimethenamid in Solutions of Bromide + Aqueous Free Chlorine

“…Analogous reports in the chlorination literature9,18,19,57,58 have attributed a second-order dependence of chlorination rates on [FAC] o to reactions with Cl 2 O. Indeed, Cl 2 O was found to be nearly 8 million times more inherently reactive than HOCl in reactions with DM 18.…”

“…An important exception is the work of Voudrias and Reinhard, 9,10 who determined Br 2 and BrCl to be a factor of 2300 and 4.9 × 10 6 , respectively, more reactive than HOBr in brominating p-xylene.…”

Formation mechanisms of trichloromethyl-containing compounds in the terrestrial environment: A critical review

“…Although the formation of Cl + can explain the kinetics of chlorination of aromatic compounds by HOCl in aqueous solution, thermodynamic arguments show that Cl + is highly unstable and therefore its concentration is likely too low to be kinetically significant (Swain and Crist, 1972). The chlorination reaction is presumably initiated by the conversion of HOCl into more reactive chlorine species such as Cl 2 or Cl 2 O (Swain and Crist, 1972;Voudrias and Reinhard, 1988;Cherney et al, 2006;Sivey and Roberts, 2012). After the addition of chlorine to the double bond, the reaction is generally followed by the addition of HO À or the elimination of H + (Deborde and von Gunten, 2008).…”