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EVIDENCE FOR NUCLEOPHILIC-ADDITION BY MUONIUM TO PYRAZINE IN WATER - CONTRAST WITH ORDINARY HYDROGEN

TitleEVIDENCE FOR NUCLEOPHILIC-ADDITION BY MUONIUM TO PYRAZINE IN WATER - CONTRAST WITH ORDINARY HYDROGEN
Publication TypeJournal Article
Year of Publication1991
AuthorsWu, Z, Barnabas, MV, Stadlbauer, JM, Venkateswaran, K, Porter, GB, Walker, DC
JournalJournal of the American Chemical Society
Volume113
Pagination9096-9099
Date PublishedNov
Type of ArticleArticle
ISBN Number0002-7863
Keywords1-HYDROPYRIDINYL RADICALS, ATOMS, ELECTRON-SPIN RESONANCE, FREE-RADICALS, LEVEL-CROSSING-RESONANCE, LIQUIDS, ORGANIC, ROTATION, SPECTROSCOPY
Abstract

The presence of heterocyclic N atoms in an aromatic solute enhance its rate of reaction toward muonium, and the free radicals formed are seen to have muonium attached to a C atom of the ring. This contrasts the behavior of H-1 in water, where addition to N-heterocyclic rings occurs an order of magnitude slower and with H attaching to N, at least in acid solution. Muonium evidently shows nucleophilic character while ordinary hydrogen atoms are electrophilic. Pyrazine (1,4-diazine) was used for this comparison with benzene because it has the advantage over pyridine of forming only two possible radicals.

URL<Go to ISI>://A1991GQ93100010