The silver nitrate oxidation of 2,2,4,6,7-pentamethylcoumaran-5-ol

Schädel, Uta; Грүнер, Маргит; Habicher, Wolf D.

doi:10.1016/s0040-4020(02)00465-9

Cited by 2 publications

(2 citation statements)

References 10 publications

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“…The hypothesized mechanisms of oxidizing NMP and subsequent reduction of silver ions are shown in Scheme . First, NMP is oxidized in the presence of heat and oxygen gas to form a peroxide species, as Drago et al also found peroxide by iodometry titration as they oxidize NMP at an elevated temperature (75 °C) and high pressure (50 psi), in the presence of oxygen. , Then peroxide transforms NMP to 5-hydroxy- N -methyl-2-pyrrolidone, and the secondary alcohol undergoes further oxidation via bimolecular elimination to form N -methyl succinimide . In the reduction of silver ions, 5-hydroxy- N -methyl-2-pyrrolidone acts as a reducing agent, which is correspondingly oxidized to N -methyl succinimide when silver is produced.…”

Section: Resultsmentioning

confidence: 99%

“…19,21 Then peroxide transforms NMP to 5-hydroxy- N-methyl-2-pyrrolidone, and the secondary alcohol undergoes further oxidation via bimolecular elimination to form N-methyl succinimide. 22 In the reduction of silver ions, 5-hydroxy-Nmethyl-2-pyrrolidone acts as a reducing agent, which is correspondingly oxidized to N-methyl succinimide when silver is produced.…”

Section: Resultsmentioning

confidence: 99%

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Understanding and Controlled Growth of Silver Nanoparticles Using Oxidized N-Methyl-pyrrolidone as a Reducing Agent

Jeon

Mack

et al. 2009

J. Phys. Chem. C

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We report a facile synthesis of silver nanoparticles (AgNPs) by using a new reducing agent, pretreated N-methyl-pyrrolidone (NMP*). The resulting AgNPs are characterized by using UV−vis, TEM, and X-ray spectroscopy. These AgNPs exhibit strong surface enhanced Raman scattering response on addition of 4-mercaptobenzoic acid. A possible redox mechanism involving silver ion and NMP* was proposed. The oxidized species resulting from thermally treated NMP/O2 were analyzed by nuclear magnetic resonance and gas chromatography techniques, and it was determined that 5-hydroxy-N-methyl-2-pyrrolidone played the role of reducing agent. The facile synthesis of functional metal nanoparticles via an environmentally friendly procedure with control in particle size, and understanding of the reaction mechanisms pave the ways to further developing metal nanoparticles for chemical and biological detections.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Understanding and Controlled Growth of Silver Nanoparticles Using Oxidized N-Methyl-pyrrolidone as a Reducing Agent

Jeon

Mack

et al. 2009

J. Phys. Chem. C

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Chiroptical Properties of Organic Radical Cations. The Electronic and Vibrational Circular Dichroism Spectra of α-Tocopherol Derivatives and Sterically Hindered Chiral Hydroquinone Ethers

2004

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Qualitatively and quantitatively reliable electronic and vibrational circular dichroism (ECD and VCD) spectra of chiral organic radical cations were obtained for the first time with R-tocopherol derivatives and sterically hindered chiral hydroquinone ethers. The isolation and spectral measurements of chiral radical cation salts were made possible by using nitrosonium or antimony derivatives as electron-transfer oxidants, which can cleanly oxidize the substrate donors without giving any byproducts in the sample solution. Such reliable ECD spectra enabled us to fully examine the chiroptical properties of organic radical cations and also compare them with those of the corresponding neutral compounds. The observed VCD spectra of neutral and radical cationic species of chiral hydroquinone ether were nicely simulated by density functional theory (DFT) calculations, from which the relative contribution of each radical cation conformer in solution was evaluated. Thus, the combined synthetic, spectroscopic, and theoretical protocol, composed of chiral modification, clean oxidation to form stable radical cations, ECD/VCD spectral analyses, and DFT calculations, was demonstrated to be a powerful, indispensable tool for elucidating a comprehensive picture of radical cationic species in solution.

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The silver nitrate oxidation of 2,2,4,6,7-pentamethylcoumaran-5-ol

Cited by 2 publications

References 10 publications

Understanding and Controlled Growth of Silver Nanoparticles Using Oxidized N-Methyl-pyrrolidone as a Reducing Agent

Understanding and Controlled Growth of Silver Nanoparticles Using Oxidized N-Methyl-pyrrolidone as a Reducing Agent

Chiroptical Properties of Organic Radical Cations. The Electronic and Vibrational Circular Dichroism Spectra of α-Tocopherol Derivatives and Sterically Hindered Chiral Hydroquinone Ethers

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