ChemInform Abstract: Oxygen Exchange as a Function of Racemization in 1‐Phenyl‐1‐ethanol. Kinetic Evidence for Ion‐Dipole Pair Intermediates.

Abstract

The rate constants for three competing processes at the chiral center in the acid‐catalyzed racemization of both (R)‐ and (S)‐1‐phenylethanol in 18O‐enriched water are determined: oxygen exchange without inversion (5.9 ±0.6), inversion without oxygen exchange (4.1 ±0.2), and oxygen exchange with inversion (7.6 ±0.7, all · 10‐4 M‐1 s‐1.