The polarisability potential as a steric index

Abstract

The acid-catalysed hydrolysis of carboxylic esters is the reference chemical reaction used for the empirical evaluation of steric effects. In this work, the polarisability potential (Hehre, et al., J. Am. Chem. Soc. 1986, 108, 1711-1712) is identified as quantum-mechanical size of substituent groups. Correlation is found between this quantity and reactivity features of the reference reaction. Copyright (C) 2010 John Wiley & Sons, Ltd.