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Issue 5, 2012
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Estimating chemical reactivity and cross-influence from collective chemical knowledge

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Abstract

Although modern chemical databases store a great wealth of structural and reactivity data, this vast “universe” of chemical information has not yet been systematically analyzed. Here, we use computers to derive from the entire body of organic-chemical knowledge the indices that estimate the reactivity and cross influence of functional groups. The major premise of our approach is that in sufficiently large and diverse collections of reactions (as the entire “history” of organic chemistry is), the frequencies with which transformations of certain groups occur, reflect their reactivities. Illustrative examples spanning several classes of reactions demonstrate that our knowledge-based indices capture the well-known reactivity trends. A free-access software is also developed with which other trends can be analyzed for various combinations of functional groups.

Graphical abstract: Estimating chemical reactivity and cross-influence from collective chemical knowledge

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Supplementary files

Article information


Submitted
04 Jan 2012
Accepted
22 Feb 2012
First published
23 Feb 2012

Chem. Sci., 2012,3, 1497-1502
Article type
Edge Article

Estimating chemical reactivity and cross-influence from collective chemical knowledge

S. Soh, Y. Wei, B. Kowalczyk, C. M. Gothard, B. Baytekin, N. Gothard and B. A. Grzybowski, Chem. Sci., 2012, 3, 1497
DOI: 10.1039/C2SC00011C

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