论文信息 - Classification of Organic Reactions: Similarity of Reactions Based on Changes in the Electronic Features of Oxygen Atoms at the Reaction Sites1

Classification of Organic Reactions: Similarity of Reactions Based on Changes in the Electronic Features of Oxygen Atoms at the Reaction Sites1

Organic reactions occur as a result of complicated interactions among many factors: structural and electronic features of reactants, reagents, catalysts, temperature, etc. In this study, organic reactions were automatically classified based on these factors. A dataset of 131 reactions was investigated focusing on the changes of electronic features on the oxygen atoms at the reaction sites by principal component analysis and self-organizing neural networks analyses. Good correlations were found between the similarities in the changes of the electronic features of oxygen atoms of the reaction sites and the similarities in the substructural transformations at the reaction sites as well as with the known reaction types. These results demonstrate that a classification based on changes of electronic features is closely related to the classifications which chemists have been establishing from various points of view. Furthermore, this indicates the possibility for the automatic and systematic classification of a...

[1] William L. Jorgensen,et al. Computer-assisted mechanistic evaluation of organic reactions. 12. pKa predictions for organic compounds in Me2SO , 1986 .

[2] Johann Gasteiger,et al. Berechnung der Ladungsverteilung in konjugierten Systemen durch eine Quantifizierung des Mesomeriekonzeptes , 1985 .

[3] Teuvo Kohonen,et al. Self-organized formation of topologically correct feature maps , 2004, Biological Cybernetics.

[4] M. G. Hutchings,et al. Quantification of effective polarisability. Applications to studies of X-ray photoelectron spectroscopy and alkylamine protonation , 1984 .

[5] T. Kohonen. Self-organized formation of topographically correct feature maps , 1982 .

[6] S. Sasaki,et al. Computer-assisted organic synthesis design and reaction prediction system, “AIPHOS” , 1988 .

[7] J. Gasteiger,et al. Knowledge Discovery in Reaction Databases: Landscaping Organic Reactions by a Self-Organizing Neural Network , 1997 .

[8] J. Gasteiger,et al. Organische Reaktionen mit Hilfe neuronaler Netze klassifiziert: Michael‐Additionen, Friedel‐Crafts‐Alkylierungen durch Alkene und verwandte Reaktionen , 1996 .