Organic Chemistry as a Language and the Implications of Chemical Linguistics for Structural and Retrosynthetic Analyses

被引:65
作者
Cadeddu, Andrea [1 ]
Wylie, Elizabeth K. [1 ]
Jurczak, Janusz [2 ]
Wampler-Doty, Matthew [1 ]
Grzybowski, Bartosz A. [1 ]
机构
[1] Northwestern Univ, Dept Chem, Dept Chem & Biol Engn, Evanston, IL 60208 USA
[2] Polish Acad Sci, Inst Organ Chem, Warsaw, Poland
关键词
chemical linguistics; graphs; information technology; retrosynthesis; symmetry;
D O I
10.1002/anie.201403708
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Methods of computational linguistics are used to demonstrate that a natural language such as English and organic chemistry have the same structure in terms of the frequency of, respectively, text fragments and molecular fragments. This quantitative correspondence suggests that it is possible to extend the methods of computational corpus linguistics to the analysis of organic molecules. It is shown that within organic molecules bonds that have highest information content are the ones that 1) define repeat/symmetry subunits and 2) in asymmetric molecules, define the loci of potential retrosynthetic disconnections. Linguistics-based analysis appears well-suited to the analysis of complex structural and reactivity patterns within organic molecules.
引用
收藏
页码:8108 / 8112
页数:5
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