Correlation of the rates of solvolysis of phenyl chloroformate

The specific rates of solvolysis of phenyl chloroformate in 21 solvents can be very well correlated using the extended Grunwald-Winstein equation, with incorporation of the N-T solvent nucleophilicity scale and the Y-Cl solvent ionizing scale, with sensitivities towards changes in the scale having values of 1.68 +/- 0.10 and 0.57 +/- 0.06, respectively. This is a solvolysis which, on the basis of several other types of evidence, is believed to follow an addition-elimination pathway with addition being rate-determining (or possibly an enforced concerted variant), and these sensitivities can be considered to be representative values for chloroformate esters following such a pathway.