APPLICATIONS OF ARTIFICIAL INTELLIGENCE FOR CHEMICAL INFERENCE .28. CONFIGURATION SYMMETRY GROUP AND ITS APPLICATION TO STEREOISOMER GENERATION, SPECIFICATION, AND ENUMERATION

The configuration symmetry group, a novel specification of the symmetry of an organic chemical structure of defined constitution, is formulated. The symmetry operations in this group are represented in part by their effects on the configurations of the stereocenters in the structure. A description follows of how this group is used: (a) to construct for the first time an algorithm that generates all the distinct stereoisomers of a chemical structure of defined constitution, (b) to specify the configuration of the stereocenters of a stereoisomer independent of geometry, and (c) to provide a general counting equation for the number of stereoisomers of a chemical structure that solves a problem dating back to van't Hoff. Several examples are provided. © 1979, American Chemical Society. All rights reserved.