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• 108-98-5 thiophenol 

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• 201799-53-3 (C₂₀H₄N₄(C₂H₅)8)Os(NO)(SC₆H₅) 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 882-33-7 diphenyldisulfane 

Relevant academic research and scientific papers

Synthesis and characterization of new aromatic thionitrites

Thionitrites (S-nitrosothiols) play an essential biological role as nitric oxide (NO.) carriers. Here, we present the synthesis, the characterization and the stability studies in solution of new aromatic thionitrites 1b-4b as potent nitric oxide donors. The four thionitrites were characterized by 1H NMR, UV-visible and IR spectroscopies. Their decomposition occurs within a few minutes in dichloromethane, and yields quantitatively the corresponding disulfide. NO. and the thiyl radicals coming from their decomposition were trapped by distinct spin traps to give characteristic EPR signals. 4b possesses the di-tert-butylphenol moiety responsible for the antioxidant properties of BHT and of the structurally-related drug probucol.

Dinitrogen tetroxide-impregnated charcoal (N2O 4/charcoal): Selective nitrosation of amines, amides, ureas, and thiols

Efficient N-nitrosation of amines, amides, and ureas, and also S-nitrosation of thiols were performed with dinitrogen tetroxide impregnated on activated charcoal (N2O4/charcoal) in CH 2Cl2 at room temperature. High selectivity was observed for N-nitrosation of dialkyl amines, N-alkylamides and N-alkylureas. Dealkylation and N-nitrosation of trialkylamines were also performed by this reagent. Copyright Taylor & Francis, Inc.

Silica-acetate complex of N2O4: A heterogeneous reagent for the selective nitration of phenols and nitrosation of thiols

Complexation of gaseous N2O4 with acylated silica gel affords an addition compound, which is an efficient heterogeneous reagent for the selective mono- and dinitration of phenol, substituted phenols and nitrosation of thiols.

Silica-polyethyleneglycols/N2O4 complexes as heterogeneous nitrating and nitrosating agents

Silica-chloride was reacted with different quantities of H(OCH2CH2)nOH (n = 2-4) to furnish silica-based linear polyethylene glycols and cyclic polyethylene glycolic ethers. The N2O4 complex of silica-tetraethylene glycolic ether (III) was selected and used as a stable, cheap, and heterogeneous silica-based reagent for the selective mono- and dinitration of phenols and nitrosation of thiols.

Silica chloride/NaNO2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions

Thiols can be readily converted to their corresponding thionitrites with a combination of silica chloride (I), wet SiO2 and sodium nitrite in dichloromethane at room temperature. Disulfides result from the homolytic cleavage of the sulfur-nitrogen bond of the unstable thionitrite and subsequent coupling of the resultant thiyl radicals.

Dinitrogen tetroxide supported on polyvinylpyrrolidone (PVP-N2O4): A new nitrosating and coupling agent for thiols and a selective oxidant for sulfides and disulfides

Gaseous N2O4 was immobilized on polyvinylpyrrolidone to give a stable polymeric reagent. Thiols were converted to S-nitrosothiols (thionitrites) using this new nitrosating agent in n-hexane or CHCl3 at 10°C. With this reagent, thiols were also converted into their corresponding disulfides. Selective oxidation of sulfides to sulfoxides and disulfides to thiosulfonates can also be achieved by this reagent at room temperature. By using an excess of the reagent, the selective one-pot synthesis of thiosulfonates from thiols at room temperature was also performed.

A kinetic study of S-nitrosothiol decomposition

Under anaerobic conditions S-nitrosothiols 1a-e undergo thermal decomposition by homolytic cleavage of the S-N bond; the reaction leads to nitric oxide and sulfanyl radicals formed in a reversible manner. The rate constants, k1, have been determined at different temperatures from kinetic measurements performed in refluxing alkane solvents. The tertiary nitrosothiols 1c (k1(69°C) = 13 × 10-3 min-1) and 1d (k1(69°C) 91 × 10-3 min-1) decomposed faster than the primary nitrosothiols 1a (k1(69°C) = 3.0 × 10-3 min-1) and 1b (k1(69°C) = 6.5 × 10-3 min-1). The activation energies (E#= 20.5 - 22.8 Kcal mol-1) have been calculated from the Arrhenius equation. Under aerobic conditions the decay of S-nitrosothiols 1a-e takes place by an autocatalytic chain-decomposition process catalyzed by N2O3. The latter is formed by reaction of dioxygen with endogenous and/or exogenous nitric oxide. The autocatalytic decomposition is strongly inhibited by removing the endogenous nitric oxide or by the presence of antioxidants, such as pcresol, β-styrene, and BHT The rate of the chain reaction is independent of the RSNO concentration and decreases with increasing bulkiness of the alkyl group; this shows that steric effects are crucial in the propagation step.

A convenient method for production of thionitrites and disulfides under mild and heterogeneous condition

Thiols can be readily converted to their corresponding thionitrite with a combination of inorganic acidic salts and sodium nitrite in dichloromethane at room temperature. Disulfides result from the homolytic cleavage of the sulfur-nitrogen bond of the unstable thionitrite and subsequent coupling of the resultant thiyl radicals.

An efficient method for production and storage of unstable S- nitrosothiols under mild and heterogeneous condition with sodium nitrite and oxalic acid dihydrate

Thiols can be readily converted to their corresponding nitrosothiols with a combination of oxalic acid and sodium nitrite in t-butanol at room temperature (26-30 °C). The reaction mixture could be solidified with decreasing its temperature to, 15 °C and w

Efficient conversion of thiols to S-nitrosothiols with the 18-crown-6 complex of N2O4 as a new nitrosating agent

Gaseous N2O4 reacts with 18-crown-6 to afford a stable ionic complex of NO+ · 18-crown-6 · H(NO3)2/-: this complex is an efficient nitrosating agent for the conversion of thiols to their co