Dynamic NMR as a Nondestructive Method for the Determination of Rates of Dissociation. XIV. Examination of Rates of Proton-Detachment from Ammonium Ions with Multiple Probes
- 1 April 1988
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 61 (4) , 1185-1190
- https://doi.org/10.1246/bcsj.61.1185
Abstract
The rates of proton-detachment and those of topomerization in ammonium ions of benzyldiethylammonium chloride and benzylisopropylmethylammonium chloride were determined by dynamic NMR spectroscopy, by taking advantage of loss of coupling of the benzylic methylene or the methyl protons for the former process and site-exchange of the diastereotopic protons at the ethyl-methylene, isopropyl-methyl, or benzylic methylene positions for the latter in 1H NMR spectroscopy. The rates of the both processes were in good agreement with each other to indicate that the rate-limiting process in the observed topomerization is the proton-detachment. Thus it is shown that any available probes may be used for the proton-detachment or for the ivestigation of the proton affinity of amines by the dynamic NMR spectroscopy in aprotic solvents. The preference of the probes was discussed.Keywords
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