Computer-assisted mechanistic evaluation of organic reactions
Abstract
CAMEO, an interactive computer program which predicts the products of organic reactions given starting materials and conditions, has been refined and extended in the area of base catalyzed and nucleophilic processes. The present capabilities of the program are outlined including brief discussions on the major segments in CAMEO: graphics, perception, and reaction evaluation. The implementation of general algorithms for predicting the acidities of a vast number of organic compounds to within 2 pK$\sb{\rm a}$ units in dimethylsulfoxide and water are then described, followed by a presentation of the reactivity rules used by the program to evaluate nucleophilic reactions. Finally, a treatment of sulfur and phosphorus ylides, iminophosphoranes, and P=X-activated anions is given illuminating the various competitions available for these reagents, such as between proton transfer and addition, 1,2- and 1,4-addition, and the Peterson, Wittig, and Horner-Emmons olefination reactions.
Degree
Ph.D.
Advisors
Jorgensen, Purdue University.
Subject Area
Organic chemistry
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