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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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Publication details

The article was received on 04 Jan 2012, accepted on 22 Feb 2012 and first published on 23 Feb 2012


Article type: Edge Article
DOI: 10.1039/C2SC00011C
Citation: Chem. Sci., 2012,3, 1497-1502
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    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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