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Molecular orbital calculations are carried out for regular trigonal bipyramidal and square pyramidal conformations of [SiHSXY]-(X = H and Y = H, OH, SH, C1, F; X = CI, F, OH, SH and Y = C1, F), where [SiHSXY]-is a proposed five-coordinated transition state for applicable nucleophilic substitution reactions of tetracoordinated silicon. The results of these calculations are correlated with experimental data on retention and inversion at silicon centers. For a given nucleophile, the experimentally established tendency toward retention in terms of leaving group (H-> OH-> SH--F > C1-) is shown