Substituent effects on chemical shifts and geminal coupling constants of benzylic protons.

Roger N. Renaud
Four series of rigid molecules were synthesized, namely, 6-substituted-phthalides, 5-substituted-3-phenylphthalans, 2-substituted-5H-dibenzo[a,d]cycloheptenes and 2-substituted-10, 11-epoxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptenes. The nuclear magnetic resonance spectrum of each compound was measured and the benzylic proton absorptions analyzed. The chemical shifts, geminal coupling constants and in some cases the vicinal and the long range coupling constants obtained from these analyses were plotted against the Hammett sigma values in each series. The rho values obtained from these plots show that the chemical shifts of...
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