COMPUTER-ASSISTED MECHANISTIC EVALUATION OF ORGANIC REACTIONS
Abstract
An interactive computer program has been developed to predict the products of organic reactions given starting materials and reaction conditions. The program has been named CAMEO, for computer-assisted mechanistic evaluation of organic reactions. In contrast to earlier approaches, analyses proceed in the forward, or synthetic, direction and the prediction of products is based upon the internal generation and evaluation of mechanistic pathways. This thesis covers various aspects of the project including ring, aromaticity, aromatic tautomer and stereochemistry perception, the stereochemistry of ionic reactions, the calculation of heats of reaction, and electrophilic aromatic substitution reactions. Organizing principles have been developed to govern electrophilic aromatic substitution reactions. Reaction analyses make use of perceptual data including rings, aromaticity, functional groups, and electrophiles. In addition, pedagogic rules for the correct manner by which to predict the products for a reacting system have been developed.
Degree
Ph.D.
Subject Area
Organic chemistry
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