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Organic Chemistry as a Language and the Implications of Chemical Linguistics for Structural and Retrosynthetic Analyses
Author(s) -
Cadeddu Andrea,
Wylie Elizabeth K.,
Jurczak Janusz,
WamplerDoty Matthew,
Grzybowski Bartosz A.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201403708
Subject(s) - retrosynthetic analysis , applied linguistics , computational linguistics , organic molecules , molecule , linguistics , chemistry , natural language processing , quantitative linguistics , computer science , computational chemistry , philosophy , stereochemistry , organic chemistry , total synthesis
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.