ArticleThe Journal of organic chemistry2018
Hydrolytic Decomposition of S-Aroylthiooximes: Effect of pH and N-Arylidene Substitution on Reaction Rate.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- A combined experimental and computational approach reveals how aromatic peptide amphiphiles self-assemble to form ion-conducting nanohelices.Materials chemistry frontiers · 2020Article
- The evolving landscape for cellular nitric oxide and hydrogen sulfide delivery systems: A new era of customized medications.Biochemical pharmacology · 2020Review
- HBiomaterials science · 2020Article
- Linker-Regulated HBiomacromolecules · 2020Article
- The Benefits of Macromolecular/Supramolecular Approaches in Hydrogen Sulfide Delivery: A Review of Polymeric and Self-Assembled Hydrogen Sulfide Donors.Antioxidants & redox signaling · 2020Review
- Supramolecular nanostructures with tunable donor loading for controlled HACS applied bio materials · 2019Article
- Supramolecular Tuning of HBiomacromolecules · 2019Article
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Authors and funding
4 authors.
Funding
Abstract
The hydrolytic decomposition of four peptides containing S-aroylthiooximes (SATOs) with variable N-arylidene substituents was investigated in 10 aqueous buffer solutions at pH values ranging from 6.0 to 10.9. UV-vis spectroscopy was employed to study the reaction kinetics, which revealed V-shaped pH-rate profiles for all peptides with a minimum near pH 8, suggesting a change from an acid-catalyzed to a base-activated reaction. Hammett plots showed positive ρ values above pH 8 and negative ρ values below pH 8, providing further evidence for a mechanism change. Based on these data, along with mass spectral evidence, we propose specific acid catalysis under mildly acidic and neutral conditions and multiple base-promoted decomposition reactions under mildly basic conditions.
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Registered trials
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