Substituent effects of phosphorus-containing groups on aromatic reactivity. Determination of substituent constants by 13C nuclear magnetic resonance spectroscopy

Abstract

13C nmr spectra have been obtained for a series of benzene derivatives substituted with phosphorus-containing groups of the type PZ2, P(O)Z2, and P(S)Z2. Inductive and resonance substituent constants were determined from the shielding of meta and para carbon atoms according to the dual-substituent parameter approach. Possible mechanisms of substituent effects of PIII and PV derived functional groups are discussed and in some cases compared with effects of the analogous nitrogen derivatives.