Conclusions With a constant nucleophile, the experimental LG order, C1-> F-SH-> OH-> H-, and tendency toward inversion, C1-> F-SH-> OH-> H-, are reflected in the context of these calculations by (1) an increase in overlap population of the Si-LG bond, CI-< F< SH-< OH-< H-(Figure 2), and (2), with the exception of SH-, a decrease in apicophilicity of the LG (Figure 3). For example, with Nu= H-, the apicophilicity decreases in the order CI-> SH-> F> OH-> ...