Deuterium-exchange Reactions with Substituted Aromatics. IV. The Poisoning Effect of Molecules Containing Nitrogen, Sulphur, or Arsenic
The catalytic exchange properties of a number of organic compounds containing nitrogen, sulfur, or arsenic were studied in the presence of benzene and heavy water. The results confirm a charge-transfer-no-bond adsorption mechanism previously proposed for the deuteration of aromatic polycyclic hydrocarbons. For aromatic nitrogen compounds an increase in ionization potential of substrate leads to an increase in deuterium incorporation and a decrease in catalyst poisoning. Some aromatic amines deuterate faster than expected by theory and this is attributed to rapid exchange of the amino hydrogens in heavy water with a consequential increase in D-H ratio at the catalyst surface. Sulfur and arsenic, even in their saturated valency states, extensively poison benzene exchange as does triethylamine. p-Benzoquinone, 2,6- dichloroquinone, and NN-dimethyl benzylamine exhibit catalytic side reactions that poison benzene exchange. With tritium oxide, the technique is suitable for the synthesis of tritiated aromatic amines and heterocycles to high specific activity.
- Research Organization:
- Originating Research Org. not identified
- Sponsoring Organization:
- USDOE
- NSA Number:
- NSA-17-039083
- OSTI ID:
- 4657217
- Journal Information:
- Australian Journal of Chemistry, Journal Name: Australian Journal of Chemistry Journal Issue: 4 Vol. 16; ISSN 0004-9425
- Country of Publication:
- Country unknown/Code not available
- Language:
- English
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Related Subjects
AMINES
AROMATICS
ARSENIC COMPOUNDS
BENZENE
BENZYL RADICALS
CATALYSIS
DEUTERIUM
DEUTERIUM COMPOUNDS
ETHYL RADICALS
HEAVY WATER
IONIZATION
ISOTOPIC EXCHANGE
LABELLED COMPOUNDS
METHYL RADICALS
ORGANIC CHLORINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PHENYL RADICALS
QUINONES
REACTION KINETICS
TRITIUM