Reactivity of phenyl N‐phenylcarbamates in the alkaline hydrolysis reaction

In the present study, we explore the application of several theoretically estimated indices that characterize the reactivity of a series of phenyl N‐phenylcarbamates in the alkaline hydrolysis reaction. The rate constants (at 25 °C) for the hydrolysis of several derivatives were spectrophotometrically determined. The obtained kinetic data in this study, combined with literature data for other derivatives, were then correlated with theoretically estimated reactivity indices: Hirshfeld and NBO atomic charges, the Parr electrophilicity index (ω), and the electrostatic potential at the carbon and oxygen atoms of the reaction centre (V_C, V_O). The predictive ability of these quantities is discussed in a comparative context. Copyright © 2011 John Wiley & Sons, Ltd.