Collect. Czech. Chem. Commun. 1990, 55, 261-272

Transmission of substituent effects in N-(p-substituted phenyl)-phthalimides

Miroslav Holík and Božena Matějková

Research Institute of Fine Chemicals, Lachema, 621 33 Brno


Chemical shifts of benzene part of the title compounds have been correlated with substituent chemical shifts (SCS) increments a for 1H and z for 13C NMR spectra. These correlations gave pieces of information not only about the through-conjugation of substituents but also about the change of the twist about the central N-C bond with the change of substituent in the para-position. In such a way the electronic effects of substituents have been studied together with the effects due to conformational changes which manifest themselves with the change in the van der Waals repulsion and/or diamagnetic anisotropy of double bond. Chemical shifts in phthalimide part of molecule have been related to the electronic effect of distant substituent after separation of the main source of variation from random error by principal component analysis.