Relative Donor-Atom Effects on Rates of Isomerization of 3-Butenenitrile Catalyzed by Anions of the Same Basicity

Article abstract of DOI:10.1021/jo00152a048

For base-catalyzed isomerization of 3-butenenitrile in Me2SO solution the order of rate constants for anions of the same basicity is ArS^->ArO^->RSO2NAr^->9-G-Fl^- (9-substituted fluorenyl carbanions).The relative rate constants vary somewhat with basicity since the Broensted β values are 0.77, 1.0, 0.82, and ca. 0.8, respectively.