Transmission of polar effects: prediction by the Kirkwood–Westheimer electrostatic field effect model

Abstract

The pKa values of four pseudo-substituted bromo- and unsubstituted 4-carboxy[2.2]paracyclophanes have been measured and Kirkwood–Westheimer calculations carried out; the substituent effects observed are both normal and reversed, the electrostatic field theory accounting for them both qualitatively and, for the pseudo ortho-, metal-, and para-isomers, quantitatively.