Reactivity of sulfur nucleophiles towards S-nitrosothiols

Munro, Andrew P.; Williams, D. Lyn H.

doi:10.1039/b004415f

Cited by 53Chemical Reaction MechanismsSynthesis and Reactivity of Sulfur-Containing CompoundsSulfur-Based Synthesis Techniques

Reactivity of sulfur nucleophiles towards S-nitrosothiols

Munro, Andrew P., Williams, D. Lyn H.·2000·Journal of the Chemical Society Perkin Transactions 2

DOI 10.1039/b004415f

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Abstract

Rate constants have been measured for the reactions of a range of S-nitrosothiols with the following sulfur-centred nucleophiles: sulfite ion, thiourea, thiocyanate ion, thiosulfate ion, thiomethoxide ion and sulfide ion. Many of the reactions were very fast and were followed in a stopped-flow spectrophotometer. For the sulfite reaction the reactive species over the pH range 4–8 was shown to be exclusively SO32−. For two RSNO species the reactivity sequence was established as: SO32− > MeS− > S2O32− ≫ SC(NH2)2 > SCN−. The reaction with sulfide ion was also rapid and generated a fairly stable yellow species (λmax 410 nm), which was probably the nitrosodisulfide ion ONSS−, but the absorbance–time data were too complex for a simple kinetic analysis. This reaction could have some potential as an analytical procedure for the determination of RSNO species. The kinetic results are discussed in terms of the factors affecting nucleophilicity and are compared with the corresponding reactions of other nitrosating species.

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Taken together, nitrite reacts with S8 and, seemingly less efficiently, with polysulfides in non-aqueous polar solvents to form products including SSNO-.
“Taken together, nitrite reacts with S8 and, seemingly less efficiently, with polysulfides in non-aqueous polar solvents leading to the formation of similar products as observed previously in the reaction of NO with sulfide [69], and nitrosothiols with thiols [70], and with sulfide [19,71] including SSNO -.”
From On the chemical biology of the nitrite/sulfide interaction (2015) · cites this paper as [71]

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Authors: Munro, A. P., & Williams, D. L. H.
Affiliations: Durham University (GB)
Venue: Journal of the Chemical Society Perkin Transactions 2
Publisher: Royal Society of Chemistry (RSC)
Published: 2000
Issue: 9
Pages: 1794-1797
ISSN: 0300-9580 (ISSN-L)
1470-1820
1364-5471
DOI: 10.1039/b004415f
OpenAlex: W2046859565
Cited by: 53
References: 10
Citations by year: 2026: 2 · 2025: 1 · 2024: 2 · 2023: 1 · 2022: 2 · 2020: 1 · 2019: 2 · 2018: 3 · 2017: 4 · 2016: 6 · 2015: 4 · 2014: 7 · 2013: 3 · 2012: 5
FWCI: 0.58
Type: journal article
Language: en
Open access: closed
Locations: Journal of the Chemical Society Perkin Transactions 2 (publishedVersion)
Funders: Engineering and Physical Sciences Research Council
Topics: Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Reactivity of Sulfur-Containing Compounds
Physical Sciences › Chemistry › Organic Chemistry › Sulfur-Based Synthesis Techniques
Keywords: S-nitrosothiols, sulfur nucleophiles, nucleophilicity, sulfite, thiourea, thiocyanate, thiosulfate, sulfide ions, reaction kinetics, rate constants, stopped-flow spectrophotometry

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Reactivity of sulfur nucleophiles towards S-nitrosothiols

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