Publication Details (including relevant citation information):
Atherton, J. H.; Blacker, J,; Crampton, M. R.; Grosjean, C. Org. Biomol. Chem., 2004, 2, 2567‐2571
Kinetics studies are reported of the reactions of benzylidene benzylamine, 4a, and of benzylidene allylamine, 4b,
with cyanide in aqueous buffers to give the corresponding a-aminonitriles. The results allow the calculation of
values of rate and equilibrium constants for reaction of the iminium ions formed from 4a and 4b with cyanide ions.
These values are compared with those, obtained from the hydrolysis reactions, for reaction of the iminium ions with
hydroxide ions and with water. Comparison with some other iminium ions reveals that those formed from 4a and 4b
are relatively unreactive due to the possibilities of charge delocalisation.