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. Author manuscript; available in PMC: 2016 Dec 1.
Published in final edited form as: Free Radic Biol Med. 2015 Oct 8;89:662–667. doi: 10.1016/j.freeradbiomed.2015.08.017

Table 2.

Reactivity of persulfides in the presence of different reductants, nucleophiles, gases, and bases. Experiments were performed anhydrously and anaerobically in CD2Cl2 at room temperature with 18 mM persulfide and reactant. All reaction products were confirmed by 1H or 31P{1H} NMR spectroscopy. S8 formation was confirmed and quantified by titration with PPh3 at the end of the reaction. Abbreviations: nr: no reaction, DTP: 1,3-dithiopropane. Reactions taking > 48 hours to occur are considered exhibit no reactivity.

Reactant TrtSSH BnSSH AdSSH
Products time Products time Products time
PPh3 TrtSH, Ph3PS < 2 min BnSH, BnSSSBn, H2S, Ph3PS 16 hr AdSH, Ph3PS > 24 hr
DTP Nr – nr – nr –
H2S(g) Nr – nr – nr –
NO(g) Nr – nr – nr –
[Na+][TrtS−] TrtSH, S8 < 2 min Polysulfides < 2 min AdSH, S8 < 2 min
[NBu4+][HS−] TrtSH, S8, H2S > 24 hr H2S, polysulfides < 2 min nr –
[NBu4+][CN−] TrtSH, S8 < 2 min H2S, BnSH, polysulfides < 2 min AdSH, S8 < 2 min
[NBu4+][AcO−] TrtSH, S8 < 2 min Polysulfides < 2 min AdSH, S8 < 2 min
[NBu4+][Cl−] TrtSH, S8 1 hr polysulfides < 2 min nr –
[NBu4+][I−] nr – polysulfides > 24 hr nr –
NEt3 TrtSH, S8 < 2 min polysulfides < 2 min AdSH, S8 30 min