1-naphthyl methyl halide와 halide ion간의 反應을 無水 acetone에서 反應 速度論的으로 연구하였다. Substrate의 softness가 현저하게 增加하면 halide ion의 nuclepphilicity가 dipolar solvent 에서도 一般的으로 $I^->Br^->CI^-$의 순서를 갖는다는 것을 보여주고 있다. Leaving group bromide일 때는 symbiotic effect에 의해서 reaction center의 softness가 증가하여 soft halide ion과의 反應이 커질 것이나 perihydrogen atom의 steric effect때문에 chloride일 때에 비해서 약간 감소하고 있다.
Kinetics of reactions of halide ions with 1-naphthyl methyl halide have been investigated in anhydrous acetone. Semi-quantitative analysis of the results shows that if the softness of the substrate increases remarkably, the nucleophilicity order of halide ions is $I^- > Br^- > Cl^-$ even in dipolar aprotic solvent. But for 1-naphthyl methyl bromide, though the reaction center which was made soft by symbiosis of bromine atom raises the reactivity of soft nucleophile, nucleophilicity order indicates that soft-soft interaction is interfered by perihydrogen.
