Oxidation of Thiols by Molecular Oxygen in Tetramethylguanidine

Wallace, Thomas J.; Jacobson, Nicholas M.; Schriesheim, A.

doi:10.1038/201609b0

Cited by 17 publications

(9 citation statements)

References 4 publications

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“…Of particular relevance to this work is the report of Oswald et al,12 in which the reactivity of alkylammonium thiolate salts in hydrocarbon solvents is reported: The acidity of aliphatic thiols (p K a = 12–14) is insufficient to allow for the isolation of their ammonium salts. However, the close association of aliphatic thiols and alkylamines is well documented,13 and Wallace et al14 demonstrated the ease with which these thiols could be oxidized by air in a tetramethylguanidine solution. These observations are relevant to this case because we were unable to isolate a salt of dodecanethiol and DBU and yet observed significant thiol oxidation rates.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of thioether derivatives of brominated poly(isobutylene‐co‐isoprene): Direct coupling chemistry for silica reinforcement

Parent¹,

White²,

Whitney³

2002

J. Polym. Sci. A Polym. Chem.

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Thioether derivatives of brominated poly(isobutylene‐co‐isoprene) (BIIR) were prepared through base‐mediated nucleophilic substitution reactions of the elastomer with thiolate ions formed in situ from thiols. The characterization of the reaction products was accomplished with studies of a model compound, brominated 2,2,4,8,8‐pentamethyl‐4‐nonene, the reactivity of which was shown to be consistent with that of the polymer. The reaction of aliphatic thiols with the allylic bromide functionality of BIIR required a strong base, and base‐catalyzed air oxidation of the thiol to disulfide operated concurrently to reduce the yield of the desired substitution products. An efficient and direct method of coupling BIIR to silica with (3‐mercaptopropyl)trimethoxysilane improved filler dispersion, thereby overcoming problematic agglomeration of reinforcing siliceous fillers in these compounds. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 2937–2944, 2002

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Section: Resultsmentioning

confidence: 99%

Synthesis of thioether derivatives of brominated poly(isobutylene‐co‐isoprene): Direct coupling chemistry for silica reinforcement

Parent¹,

White²,

Whitney³

2002

J. Polym. Sci. A Polym. Chem.

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“…These results indicate the inherent instability of LNH 2 and LN 3 , which is likely due to the interaction between the amine moiety and the thiols. 26,27 On the other hand, LOMe and LCOOH are stable and do not undergo spontaneous oxidation ( Fig. 1c and ESI, † SI2) over the same observation period.…”

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confidence: 76%

Stable DHLA–PEG capped PbS quantum dots: from synthesis to near-infrared biomedical imaging

et al. 2018

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The short shelf-life of water-soluble quantum dots (QDs) due to colloidal instability represents a major drawback to their exploitation. This work examines the colloidal stability of PbS nanoparticles capped with dihydrolipoic acid–polyethylene glycol (DHLA–PEG) ligands terminated with functional groups such as –NH2, –COOH, OMe and –N3.\ud and their application for in vivo imaging. We prove a mechanism of colloidal instability and develop a strategy to produce for the first time stable PEG-capped PbS quantum dots with high quantum yield and optical emission in the first and the second near-infrared (NIR) windows of low absorption of biological tissues. The NIR imaging of in vivo\ud biodistribution is demonstrated at wavelengths 41000 nm, with benefits of reduced tissue absorption and light scattering. The stability, biocompatibility and potential for further QD functionalization open up realistic prospects for non-invasive bioimaging applications

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“…Peroxide anions of this type have been postulated as possible intermediates in the anionic oxidation of 2-nitropropane.16 A second possible mode of reaction would be direct transfer of an electron to oxygen (eq. 3), reac-ArCH2~A 02 -ArCH2• A 02 (3) (15) G. A. Russell, J. Am.…”

Section: Discussion Of Resultsmentioning

confidence: 99%

Solvent Effects in the Oxidation of Sulfur Compounds. The Base-Catalyzed Oxidation of Alkylthiophenes

Wallace¹,

Baron²

1965

J. Org. Chem.

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Oxidation of Thiols by Molecular Oxygen in Tetramethylguanidine

Cited by 17 publications

References 4 publications

Synthesis of thioether derivatives of brominated poly(isobutylene‐co‐isoprene): Direct coupling chemistry for silica reinforcement

Synthesis of thioether derivatives of brominated poly(isobutylene‐co‐isoprene): Direct coupling chemistry for silica reinforcement

Stable DHLA–PEG capped PbS quantum dots: from synthesis to near-infrared biomedical imaging

Solvent Effects in the Oxidation of Sulfur Compounds. The Base-Catalyzed Oxidation of Alkylthiophenes

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