ISSN:
0538-8066
Keywords:
Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The reactions of the title substrate with a series of secondary alicyclic amines are subjected to a kinetic study in 44 wt% aqueous ethanol, 25.0°C, and ionic strength 0.2 M (KCl). The Brönsted-type plot (log kN vs. pKa of the amine, where kN is the second-order rate coefficient) obtained is linear with slope β = 0.53, which indicates a concerted mechanism. The predicted Brönsted break for a hypothetical stepwise mechanism is pKa0 = 8.7, which was not observed (pKa range of amines: 6-11). The same reaction in water is stepwise, which shows that the tetrahedral intermediate found in water is much destabilized by the change of solvent from water to aqueous ethanol. © 1994 John Wiley & Sons, Inc.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/kin.550260510
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