Journal article
Kinetics and mechanism of N-H and C-H isotopic exchange in pyrrole and indole: Acid-catalysed exchange in aqueous acetonitrile solutions
Journal of the Chemical Society, Perkin Transactions 2, (12), pp.1316-1320
1975
Abstract
The deuteriodeprotonation of the N–H and of the α- and β-C–H positions in pyrrole, and of the N–H and β-C–H positions in indole, has been studied kinetically as a function of the concentration of perchloric acid, medium composition, and temperature in aqueous (2H2O) acetonitrile solutions. The N–H exchange process was followed using the first overtone of the N–H stretching mode. Ancillary i.r. studies define the molecular states of the reactants. The Hammett H0 acidity function is reported for dilute perchloric acid in acetonitrile-water mixtures. Bunnett w values clarify differences between the hydration of the N–H and C–H exchange transition states.
Details
- Title
- Kinetics and mechanism of N-H and C-H isotopic exchange in pyrrole and indole: Acid-catalysed exchange in aqueous acetonitrile solutions
- Authors/Creators
- D.M. Muir (Author/Creator)M.C. Whiting (Author/Creator)
- Publication Details
- Journal of the Chemical Society, Perkin Transactions 2, (12), pp.1316-1320
- Publisher
- Chemical Society
- Identifiers
- 991005545393707891
- Murdoch Affiliation
- Murdoch University
- Language
- English
- Resource Type
- Journal article
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