The Sn Mechanism in aromatic compounds. 24. The positional order of inductive effects in the aromatic ring.

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Abstract
The two main views on the transmission of the inductive (I) effect within the ring are tested by comparison of the reactivity of the chlorine in 2-, 3-, and 4-chloro-N-methylpyridinium salts with sodium p-nitrophenoxide in absolute methanol. Activation by the ring N+, corresponding to Cб+ for attached -I groups, is shown to be in the positional order : 2>4>>3. The corresponding rate ratios (at 50 °C) are 4.89 x 107 : 1.62 x 106 : 1. These results strongly favour the view that both σ- and π-electron systems are involved in the intra-annular transmission. Similar results are obtained for reaction with sodium methoxide in absolute methanol.

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