Activation energy nucleophilic aliphatic substitution

The effects of several cationic and anionic surfactants on the nucleophilic aliphatic substitution reaction between thiosulfate ion and sodium bromoacetate (see Table 16) have been investigated by Erikson and Lingafelter (1955) and Sebba and Wiggill (1966). The reaction in the presence of anionic surfactants was influenced only slightly by micelliza-tion whereas dodecyltrimethylammonium bromide and CTAB accelerated the reaction by factors of 1-6 and 4-3 respectively. In the latter case the rate acceleration was found to be the consequence of a decrease in the energy of activation (Sebba and Wiggill, 1966). 

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