2023
DOI: 10.1002/anie.202313187
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Synergistic Activation of Nitrite and Thiocarbonyl Compounds Affords NO and Sulfane Sulfur via (Per)thionitrite (SNO/SSNO)

Gayathri Kolliyedath,
Tuhin Sahana,
Silpa Mary Johnson
et al.

Abstract: (Per)thionitrite (SNO–/SSNO–) intermediates play vital roles in modulating nitric oxide (NO) and hydrogen sulfide (H2S) dependent bio‐signalling processes. Whilst the previous preparations of such intermediates involved reactive H2S/HS– or sulfane sulfur (S0) species, the present report reveals that relatively stable thiocarbonyl compounds (such as carbon disulfide (CS2), thiocarbamate, thioacetic acid, and thioacetate) react with nitrite anion to yield SNO–/SSNO–. For instance, the reaction of CS2 and nitrite… Show more

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Cited by 4 publications
(1 citation statement)
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“…While the interactions of EbSe with various ROS (such as peroxides, peroxynitrite, and hydroxyl radical) were previously assessed computationally, 4–6,11 the reactivity of nitrite anion ( ONO − ) with ebselen ( EbSe )/ebsulfur ( EbS ) is not known to the best of our knowledge. Inspired by our recent work on the generation of reactive intermediates from the reaction of nitrite anion and organosulfur compounds, 13 the objective of this work is to probe the interactions/reactions between EbSe/EbS and ONO − using in-depth NMR spectroscopic and computational analyses. This work reveals that the noncovalent interactions in the resultant adduct complex EbSe⋯ONO − amplify the reactivity of the otherwise stable nitrite anion towards aromatic amines (Fig.…”
mentioning
confidence: 99%
“…While the interactions of EbSe with various ROS (such as peroxides, peroxynitrite, and hydroxyl radical) were previously assessed computationally, 4–6,11 the reactivity of nitrite anion ( ONO − ) with ebselen ( EbSe )/ebsulfur ( EbS ) is not known to the best of our knowledge. Inspired by our recent work on the generation of reactive intermediates from the reaction of nitrite anion and organosulfur compounds, 13 the objective of this work is to probe the interactions/reactions between EbSe/EbS and ONO − using in-depth NMR spectroscopic and computational analyses. This work reveals that the noncovalent interactions in the resultant adduct complex EbSe⋯ONO − amplify the reactivity of the otherwise stable nitrite anion towards aromatic amines (Fig.…”
mentioning
confidence: 99%