The standard free energy change for formation of R+X–(aq) from RX(aq) is so high in the case of R = Me and Et that primary alkyl halides are unlikely to undergo nucleophilic substitution by the ion-pair mechanism; this mechanism is slightly unfavourable for the case of R = Pri, but is energetically feasible for the t-butyl halides.
M. H. Abraham, J. Chem. Soc., Chem. Commun., 1973, 51 DOI: 10.1039/C39730000051
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