title: Organic chemistry as a language and the implications of chemical linguistics for structural and retrosynthetic analyses.
abstract: 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.
authors.affiliation: Department of Chemical and Biological Engineering, Department of Chemistry, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208 (USA) http://dysa.northwestern.edu.
authors.forename: Andrea
authors.initials: A
authors.lastname: Cadeddu
authors.forename: Elizabeth K
authors.initials: EK
authors.lastname: Wylie
authors.forename: Janusz
authors.initials: J
authors.lastname: Jurczak
authors.forename: Matthew
authors.initials: M
authors.lastname: Wampler-Doty
authors.forename: Bartosz A
authors.initials: BA
authors.lastname: Grzybowski
keywords: chemical linguistics; graphs; information technology; retrosynthesis; symmetry