Abstract
The sulphonation of a series of sulphonic acids of the general structure Ph[CH2]nSO3H (n= 1,2,3–6) in concentrated aqueous sulphuric acid at 25 °C has been studied, and partial rate factors are reported. With benzenesulphonic acid the SO3H substituent exhibits a –M effect in addition to the combined inductive and direct field effect. The results of the ω-phenylalkane-1-sulphonic acids are explained in terms of the competing deactivating effect of the SO3H group (a combined relayed inductive and direct field effect) and the activating hyperconjugative electron release of the benzylic CH2 group. The former effect decreases with increasing n, whereas the latter effect only slightly increases upon increasing n from 1 to 2.As judged from a comparison with the fp of the sulphates of the general structure Ph[CH2]nOSO3H (n 2) the electronic effects of the [CH2]nOSO3H and the [CH2]nSO3H groups are about the same.
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