Steric inhibition of synergistic radical stabilizing effects

FG Bordwell, MJ Bausch, JP Cheng…

Index: Bordwell, F. G.; Bausch, Mark J.; Cheng, Jin-Pei; Cripe, Thomas H.; Lynch, Tsuei-Yun; Mueller, Mark E. Journal of Organic Chemistry, 1990 , vol. 55, # 1 p. 58 - 63

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Citation Number: 10

Abstract

Equilibrium acidities in Me2S0 for 14 aN-morpholinyl-, 6 aN-piperidinyl-, and 7 a- cyclohexylarylacetonitriles and the oxidation potentials of their conjugate bases have been determined. The increased pKm values by about 2 units observed in these systems, relative to the corresponding arylacetonitriles, is ascribed to the presence of increased steric constraints in the anions. Hammett plots revealed larger p values than for arylacetonitriles ...