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Research Article

A Novel Method for Characterization of Three-Dimensional Reaction Fields Based on Electrostatic and Steric Interactions toward the Goal of Quantitative Analysis and Understanding of Organic Reactions

Hiroko Satoh,*^†^‡ Sachiko Itono,^§ Kimito Funatsu, Keiko Takano,^§ and Tadashi Nakata^†

Synthetic Organic Chemistry Laboratory, The Institute of Physical and Chemical Research (RIKEN), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan, PRESTO, Japan Science and Technology Corporation, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan, Department of Chemistry, Faculty of Science, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan, and Department of Knowledge-Based Information Engineering, Toyohashi University of Technology, 1-1 Tempaku, Toyohashi, Aichi 441-8580, Japan

J. Chem. Inf. Comput. Sci., 1999, 39 (4), pp 671–678

DOI: 10.1021/ci9801567

Publication Date (Web): June 2, 1999

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

†

RIKEN.

‡

PRESTO.

Ochanomizu University.

Toyohashi University of Technology.

Abstract

A novel characterization method named FRAU (Field-characterization for reaction analysis and understanding), which numerically characterizes field around molecules based on electrostatic and steric interactions with pseudoreactant, has been developed for giving numeric measures of factors controlling reactions. FRAU estimates three kinds of features (FRAU features), i.e., extent of reaction field, electrostatic features, and steric features. Power of the FRAU features as discriminators recognizing similarities and differences of characteristics of structures and roles of reagents in reactions have been examined by 39 reagents containing Mg or B atoms. Similarities in these features were analyzed with the help of a self-organizing map (SOM). Good correspondences were found between the features, structures, and the role of the reagents in reaction. The results show abilities of FRAU to give useful numeric characterization of reagents.

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