It is widely accepted that dipole-dipole interactions in the S(N)2 transition Structure can play a dominant role in determining reaction rates. A model of this type was proposed some years ago to explain the remarkably low reactivity of galactopyranose-6-O-sulfonates toward S(N)2 displacement, and similar arguments have recently been restated in the context of gas-phase reactions. In this paper, we present ab initio calculations (B3LYP/ 6-31+G(d,p)) on model structures and an analysis of charge densities using the theory of atoms in molecule's. We find that the maximum possible impact of local dipole-dipole interactions is insufficient to account for the observed reactivity differences.