An Investigation into the Nature of π-Inductive Effects: π Polarization Effects in Phenylalkanes with Polar or Charged Substituents

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Abstract
PH dependent 13C chemical shifts for phenylglycine, phenylalanine, and phenylalanyl derivatives demonstrate that the electronic distribution of the phenyl group depends upon the distance of charged groups from the phenyl ring. The pattern of chemical shifts and the results of CNDO/2 MO calculations indicate that this is due to polarization of the phenyl π electron system. 13C chemical shifts and CNDO/2 calculations for α- and β-substituted phenylalkanes (substituent = NH3+, Cl or Br) provide further evidence for a π polarization effect.

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