text: Localized electronic effects are a combination of inductive and field effects. Due to the similarity in these effects, it is difficult to separate their contributions to the electronic structure of a molecule. There is, however, a large body of literature devoted to developing an understanding of the relative significance of induction and field effects by analyzing related compounds in an attempt to quantify each effect based on the present substituents and molecular geometry. For example, the three compounds to the right, all octanes, differ only in the number of linkers between the electron withdrawing group X and an acidic functional group, which are approximately the same spatial distance apart in each compound. It is known that an electron-withdrawing substituent will decrease the pKa of a given proton (i.e. increase the acidity) inductively. If induction was the dominant effect in these compounds, acidity should increase linearly with the number of available inductive pathways (linkers). However, the experimental data shows that effect on acidity in related octanes and cubanes is very similar, and therefore the dominant effect must be through space.
  In the cis-11,12-dichloro-9,10-dihydro-9,10-ethano-2-anthroic acid syn and anti isomers seen below and to the left, the chlorines provide a field effect. The concentration of negative charge on each chlorine has a through space effect which can be seen in the relative pKa values. When the chlorines are pointed over the carboxylic acid group, the pKa is higher because loss of a proton is less favorable due to the increase in negative charge in the area. Loss of a proton results in a negative charge which is less stable if there is already an inherent concentration of electrons. This can be attributed to a field effect because in the same compound with the chlorines pointed away from the acidic group the pKa is lower, and if the effect were inductive the conformational position would not matter.