Kinetic isotope effects involving deuterated aniline nucleophiles

Deuterium kinetic isotope effects (KIE) are normally studied with deuteriated substrate molecules in organic reactions such as nucleophilic substitution and β-elimination. We report here a novel approach to the characterization of transition state (TS) structures by deuterium KIE using deuteriated nucleophiles. Primary and secondary α-deuterium kinetic isotope effects are observed with deuteriated aniline nucleophiles in the SN2 reactions of 1-phenylethyl and benzyl benzenesulphonates, providing evidence in support of the four centre transition state mechanism for the former reaction. (author)