Cathodic reduction of pyridine in liquid ammonia

Brown, O.R.; Butterfield, R.J.; Millington, J. P.

doi:10.1016/0013-4686(82)80094-7

Cited by 11 publications

(3 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For both phen and bath, a two‐successive reduction wave was observed. Such a wave can be seen for some azines, and the first reduction wave may involve dimerization of the anions ,. For the N‐donor ligands, the oxidation peak currents are much smaller than the reduction ones.…”

Section: Resultsmentioning

confidence: 96%

Electrogenerated Chemiluminescence and Electronic States of Several Organometallic Eu(III) and Tb(III) Complexes: Effects of the Ligands

et al. 2019

View full text Add to dashboard Cite

We report the electrochemical properties, and electrogenerated chemiluminescence (ECL) of eight different organometallic complexes of Eu(III) and Tb(III), Eu(dbm)3phen, Eu(dbm)3bath, Eu(fod)3phen, Eu(tta)3phen, Tb(acac)3phen, Tb(acac)3bath, Tb(fod)3phen, and Tb(tmhd)3bpy in acetonitrile, where phen, bath, and bpy are 1, 10‐phenanthroline, bathophenanthroline, 2,2′‐bipyridyl, respectively, and the anionic ligands, acac−, dbm−, fod−, and tta− are the enolate forms of acetylacetone, dibenzoylmethanate, 6,6,7,7,8,8,8‐heptafluoro‐2,2‐dimethyl‐3,5‐octanedione, and thenoyltrifluoroacetone, respectively. The electronic states of the neutral and some charged states of the complexes were clarified with density functional theory calculations. The ECL spectra were recorded by using S2O82− as a coreactant, and for all complexes, sharp ECL spectra, which are attributable to the f‐f transitions, were observed. On the potential‐dependent ECL spectra, broad ECLs, which were originated from the ligands, were also detected. Based on the ECL behavior and the electronic states, the mechanisms of the intraconfigurational ECL were discussed.

show abstract

Section: Resultsmentioning

confidence: 96%

Electrogenerated Chemiluminescence and Electronic States of Several Organometallic Eu(III) and Tb(III) Complexes: Effects of the Ligands

et al. 2019

View full text Add to dashboard Cite

show abstract

“…The half-wave potential for the reduction of Py over a Pt electrode in DMF is -2.7 V vs Ag/AgCl 40 while in liquid NH 3 this potential is -2.1 V. 41 Let us assume that Py starts to be reduced in BMIPF 6 at -1.6 V vs PQRE, where the new SERS features emerge. This potential is equivalent to -1.2 V vs Ag/ AgCl, i.e., too far from the reduction potentials mentioned above.…”

Section: Resultsmentioning

confidence: 99%

“…The half-wave potential for the reduction of Py over a Pt electrode in DMF is −2.7 V vs Ag/AgCl while in liquid NH 3 this potential is −2.1 V . Let us assume that Py starts to be reduced in BMIPF 6 at −1.6 V vs PQRE, where the new SERS features emerge.…”

Section: Resultsmentioning

confidence: 99%

Surface-Enhanced Raman Scattering at the Silver Electrode/Ionic Liquid (BMIPF₆) Interface

et al. 2006

View full text Add to dashboard Cite

This is the first report of in situ SER spectra of chemical species adsorbed on a Ag/room temperature ionic liquid (RTIL) interface. We have investigated the dependence of the SERS intensity of the RTIL derived from 1-n-butyl-3-methylimidazolium hexafluorophosfate (BMIPF6) adsorbed on a silver electrode. It has been shown that the BMI+ adsorbs on the silver electrode for potentials more negative than -0.4 V vs a Pt quasireference electrode (PQRE). In the -0.4 to -1.0 V potential range the SER spectra are similar to the Raman spectrum of the RTIL BMIPF6. At potentials more negative than -1.0 V some imidazolium ring vibrational modes and N-CH3 vibrations are enhanced, suggesting that the imidazolium ring is parallel to the surface and for potentials <-2.8 V the BMI+ is reduced to the BMI carbene. The potential dependence of the SERS intensities of Py adsorbed on a silver electrode in BMIPF6 has also been investigated. The results have shown that at potentials less negative than -0.8 V (vs PQRE) Py adsorbs at an end-on configuration forming an Ag-N bond. In the -0.9 to -1.4 V potential range Py molecules lie flat on the electrode surface and at potentials <-1.4 V Py is replaced by the BMI+. The electrochemical and SERS results have shown that Py has the effect of changing the oxidation of silver in that medium as well as the reduction of BMI+ to the BMI carbene. In the presence of Py the BMI+ reduction is observed at potentials near -2.4 V. The Ag electrode has presented SERS activity from 0.0 to -3.0 V.

show abstract

TheBirch Reduction of Aromatic Compounds

Rabideau

Marcinow²

1992

Organic Reactions

131

138

View full text Add to dashboard Cite

The reduction of aromatic compounds by alkali metals in liquid ammonia represents an important method for the preparation of partially unsaturated six‐membered rings. The reaction was discovered by Wooster and Godfrey, but the major development resulted from the efforts of A. J. Birch, and the reaction has since come to bear his name. Although a variety of metals can be used, the most common are sodium and lithium, and, to a lesser extent, potassium. Cosolvents such as ether or tetrahydrofuran (THF) are often used to improve solubility, and weak acids such as alcohols may be employed during the reaction as proton sources. The latter are necessary for the reduction of benzene and its unactivated derivatives. Improvement in experimental procedures by Wilds and Nelson, the application to polynuclear compounds by Hückel and later by Harvey, and the development of methods for the alkylation of the anions generated in this process (i.e., reductive alkylation) have made this reaction an important approach to the synthesis of a wide variety of organic compounds.

show abstract

Cathodic reduction of pyridine in liquid ammonia

Cited by 11 publications

References 27 publications

Electrogenerated Chemiluminescence and Electronic States of Several Organometallic Eu(III) and Tb(III) Complexes: Effects of the Ligands

Electrogenerated Chemiluminescence and Electronic States of Several Organometallic Eu(III) and Tb(III) Complexes: Effects of the Ligands

Surface-Enhanced Raman Scattering at the Silver Electrode/Ionic Liquid (BMIPF₆) Interface

TheBirch Reduction of Aromatic Compounds

Contact Info

Product

Resources

About

Cathodic reduction of pyridine in liquid ammonia

Cited by 11 publications

References 27 publications

Electrogenerated Chemiluminescence and Electronic States of Several Organometallic Eu(III) and Tb(III) Complexes: Effects of the Ligands

Electrogenerated Chemiluminescence and Electronic States of Several Organometallic Eu(III) and Tb(III) Complexes: Effects of the Ligands

Surface-Enhanced Raman Scattering at the Silver Electrode/Ionic Liquid (BMIPF6) Interface

TheBirch Reduction of Aromatic Compounds

Contact Info

Product

Resources

About

Surface-Enhanced Raman Scattering at the Silver Electrode/Ionic Liquid (BMIPF₆) Interface