Construction of a Statistical Evaluation Model Based on Molecular Centrality to Find Retrosynthetically Important Bonds in Organic Compounds

• Published in: European Journal of Organic Chemistry 2008-12, Vol.2008 (35), p.5995-6007
• Main Authors: Tanaka, Akio, Kawai, Takashi, Matsumoto, Tsutomu, Fujii, Mihoko, Takabatake, Tetsuhiko, Okamoto, Hideho, Funatsu, Kimito
• Format: Article
• Language: English
• Subjects: Bond centrality; Bond dissociation energy; Molecular centrality; Molecular complexity; Retrosynthesis; Synthesis design
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200800392

For the purpose of finding retrosynthetically important bonds in a molecule, a new evaluation score has been defined through a logistic regression analysis of known reactions stored in reaction databases. We conceived that reaction center bonds in reaction databases describe one of the most retrosynthetically important bonds for each product structure. The derived statistical equation consists of bond centrality and bond dissociation energy terms. The equation shows that synthetically useful bonds tend to be more central in a molecule and to be weaker bonds. Coefficients in two statistical equations derived from two different reaction data sets are quite similar to each other. From a comparison of molecular complexities and validation with 35 complicated organic compounds, the evaluation equation was proved to be useful. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) The evaluation equation to determine retrosynthetically important bonds has been constructed from reaction databases bylogistic regression analysis. The equation consists of bond centrality and bond dissociation energy terms.