Hydrogen isotope exchange reactions involving C–H (D, T) bonds

Junk, Thomas; Catallo, W. James

doi:10.1039/cs9972600401

Cited by 276 publications

(150 citation statements)

References 26 publications

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“…[57][58][59] Deuterated molecules can be used in stable isotopic tracer studies where they can be detected using mass spectrometry. Furthermore, deuterium labeling provides a route to obtain tritium labeled molecules for radiotracer studies.…”

Section: Characterization and Investigation Into The Formation Of Dmamentioning

confidence: 99%

Preparation and Characterization of 4-Dimethylaminopyridine-Stabilized Palladium Nanoparticles

2007

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Abstract.DMAP stabilized palladium nanoparticles with a mean diameter of 3.4 0.5 nm are prepared from the aqueous phase reduction of Na 2 PdCl 4 using NaBH 4 in the presence of DMAP. TEM and UV-Vis spectroscopy characterization of the nanoparticle dispersion shows no obvious change in the nanoparticles several months after preparation.1 H NMR spectroscopy of the nanoparticles shows that the nanoparticle dispersion also contains a boron/DMAP complex and two palladium/DMAP complexes. One of the palladium complexes crystallizes out of the dispersion and is identified as Pd(DMAP) 4 (OH) 2 by X-Ray Crystallography. Following extensive analysis it is believed that the palladium/DMAP complexes are formed following the oxidation of the palladium nanoparticles. The prepared nanoparticle dispersion promotes selective hydrogen/deuterium (H/D) exchange on the carbon atoms to the endocyclic nitrogen atom on the DMAP stabilizing ligands through reaction with D 2 O. This activity is attributed to the presence of the nanoparticles rather than to the presence of the oxidized palladium/DMAP complexes.

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Section: Characterization and Investigation Into The Formation Of Dmamentioning

confidence: 99%

Preparation and Characterization of 4-Dimethylaminopyridine-Stabilized Palladium Nanoparticles

2007

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“…3D values of natural hydrocarbons have been used for exploration and paleoenvironmental reconstruction. However, we now recognize that hydrogen from water chemically participates in the thermal maturation of organic matter (Siskin and Katritzky, 1991;Price, 1994;Seewald et al, 1998), and becomes part of organic hydrogen (Hoering, 1984;Lewan, 1993Lewan, , 1997Seewald, 1994;Stalker et al, 1995Stalker et al, , 1998Junk and Catallo, 1997;Seewald et al, 1998;ACS, 1999;Schimmelmann et al, 1999;Leif and Simoneit, 2000). This challenges us to re-evaluate experimentally the utility of D/H ratios in thermally matured fossil fuels and formation waters for exploration and paleoenvironmental reconstructions.…”

Section: Introductionmentioning

confidence: 99%

Experimental controls on D/H and 13 C/ 12 C ratios of kerogen, bitumen and oil during hydrous pyrolysis

Schimmelmann

Boudou

Lewan

et al. 2001

Organic Geochemistry

129

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Large isotopic transfers between water-derived hydrogen and organic hydrogen occurred during hydrous pyrolysis experiments of immature source rocks, in spite of only small changes in organic 13 C/ 12 C. Experiments at 330'C over 72 h using chips or powder containing kerogen types I and III identify the rock/water ratio as a main factor affecting ASD for water and organic hydrogen. Our data suggest that larger rock permeability and smaller rock grain size increase the H-isotopic transfer between water-derived hydrogen and thermally maturing organic matter. Increasing hydrostatic pressure may have a similar effect, but the evidence remains inconclusive.

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“…Pd/C catalysts have previously been used [11] to catalyse H-D exchange at activated sites within benzylic compounds using D 2 as a deuterium source while Pd/C and Pt/C have been used synergistically [12,13] to catalyse such reactions on activated and sterically-hindered sites using D 2 O.…”

Section: Introductionmentioning

confidence: 99%

“…The ability to selectively label molecules with deuterium is extremely important in pharmacological, chemical and environmental research especially in the investigation of reaction mechanisms [1] and kinetics [2] of carbon hydrogen bond activation processes. Deuterated molecules can also be used in stable isotopic tracer studies for use in GC or LC MS internal standardisation as well as in more specialist applications such as the development of non-linear optical materials [3].…”

Section: Introductionmentioning

confidence: 99%

Selective H–D exchange catalysed by aqueous phase and immobilised Pd nanoparticles

Sullivan¹,

Flanagan²,

Hain³

2008

Catalysis Today

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Publication informationCatalysis Today, 139 (3): 154-160Publisher Elsevier Item record/more information http://hdl.handle.net/10197/4001 Publisher's statementThis is the author's version of a work that was accepted for publication in Catalysis Today. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Catalysis Today, 139 (3) We have studied the effect of several different variables on the rate of the selective H-D exchange activity for a model pyridine, i.e. 4-Dimethylaminopyridine (DMAP).These variables include temperature, nanoparticle aging, nanoparticle re-reduction with H 2 and nanoparticle immobilisation onto multi-walled carbon nanotubes (MWCNT). We have also extended the study to related pyridine containing molecules.

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Hydrogen isotope exchange reactions involving C–H (D, T) bonds

Cited by 276 publications

References 26 publications

Preparation and Characterization of 4-Dimethylaminopyridine-Stabilized Palladium Nanoparticles

Preparation and Characterization of 4-Dimethylaminopyridine-Stabilized Palladium Nanoparticles

Experimental controls on D/H and 13 C/ 12 C ratios of kerogen, bitumen and oil during hydrous pyrolysis

Selective H–D exchange catalysed by aqueous phase and immobilised Pd nanoparticles

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