This paper continues our investigation into a simple dipole-dipole interaction model proposed to explain the dramatically reduced S(N)2 reactivity at the primary C6 position of galacto-configured pyranose systems relative to their gluco isomers. We present ab initio calculations (B3LYP/6-31+G(d,p)) on six model structures that show that this effect is not a major influence. Reactant rotameric equilibria as well as free-energy reaction barriers and reaction path curvature were evaluated. Results point to a number of other factors that could account for the observed reactivity differences. Our results cast doubt on the general relevance of transition structure dipole-dipole repulsions to S(N)2 reactivity.