Computer-assisted organic synthesis planning: effective bond polarity as a guideline to reactivity

A first section involved in reactivity prediction has been introduced in a program for computer-aided organic synthesis planning. The concepts of native polarity, induced polarity, and effective polarity have been used to determine the best elecronic state for the retrosynthetic breakage of strategic bonds. The characterization obtained is used to suggest the most feasible reactive behavior for the atoms spanning the strategic bond. The procedure and the atomic and molecular physical properties used in the determination of the polarities are described. The logical component is intruduced to extend the number of bonds meaningfully treated by the procedure. Results obtained show the low number of bonds that remain unresolved by the semirecursive program logic.