THE BAKER–NATHAN EFFECT OBSERVED IN THE RELATIVE RATES OF REDUCTION OF SEVERAL PARA-ALKYLATEDNITROBENZENES BY SODIUM HYDROSULPHIDE

Abstract

By measuring the initial rates of production of hydrodisulphide during reductions by sodium hydrosulphide in aqueous ethanol, it has been shown that the relative rates of reduction of a number of para-alkylated nitrobenzenes are in the order p-H- > p-t-butyl- > p-isopropyl- = p-cyclohexyl- > p-ethyl- > p-methyl-nitrobenzene. This is in accord with the "hyperconjugative" order of electron release by these alkyl groups.