Table 2. Second-order rate constants (±S.D., n≥4) for the reaction of HOCl with glycosamine monosaccharides and polymer-derived glycosamine residues at pH 7.4, and structural assignment of product chromophores.

Substrate	k2 (37 °C) (M−1·s−1)	Product λmax (nm)	Assigned structure of product
GlcNH2	1.76×106*	258	Chloramine (R-NCl-H)
GlcNH2 chloramine	∼33†	∼300	Dichloramine (R-NCl2)
GlcNSO3	0.91±0.13‡	272	N-chlorosulphonamide (R-NCl-SO3−)
GlcNAc	0.064±0.003§	<220	Chloramide (R-NCl-C(O)CH3)
Polymer-derived GlcNH2	3.1×105∥	254	Chloramine (R-NCl-H)
Polymer-derived GlcNH2 chloramine	∼9¶	318	Dichloramine (R-NCl2)
Polymer-derived GlcNSO3	0.051±0.02	272	N-chlorosulphonamide (NCl-SO3−)
Polymer-derived GlcNAc	0.012±0.03	<220	Chloramide (R-NCl-C(O)CH3)

* Estimated from k₂ (9.5 °C)=(3.5±0.1)×10⁵·M⁻¹·s⁻¹ (see text); k₂ (22 °C, estimate)=7.6×10⁵·M⁻¹·s⁻¹.

† Estimated from k₂ (22 °C)∼14 M⁻¹·s⁻¹ (see text).

‡ k₂ (22 °C)=0.062±0.01 M⁻¹·s⁻¹.

§ k₂ (22 °C)=0.0108±0.0002 M⁻¹·s⁻¹.

∥ Estimated from k₂ (10 °C)=(6.4±0.1)×10⁴ M⁻¹·s⁻¹ (see text).

¶ Estimated from k₂ (22 °C)∼4 M⁻¹·s⁻¹ (see text).