Computer software to predict the effect a functional group has on another within the same molecule

Every synthetic chemist knows that a functional group in one part of a molecule can have an influence on the reactivity of other functional groups within the molecule, or impact upon the feasibility of a reaction. Now, researchers from the US have delved into the history of organic chemistry to help chemists better predict the effect that functional groups will have on one another within a molecule.   

Traditionally, chemists have had to rely on the information contained in books, journals, databases or, commonly, personal experience in order to estimate the effect one functionality will have on another. However, the reliance on these sources may soon be a thing of the past thanks to Bartosz Grzybowski and his colleagues from Northwestern University, Illinois, who have extracted reactions recorded in the scientific literature to gain a better understanding of their complex interactions. 


The software is called ChemGPS and it can help to rapidly establish knowledge-based reactivity and structural trends

By using advanced software and computational techniques, the researchers were able to look at around 7 million unique reactions and around 7 million substances from the organic chemistry literature dating back to 1779. Using this data, they designed software that is able to predict whether one functional group will activate or deactivate another functional group in the same molecule. Such useful information could, in the future, allow researchers to better decide which reactants are the most appropriate to use in their synthesis, saving both time and money.   

Organic chemist Jonathan Goodman from the University of Cambridge, UK, thinks that ’analyses of databases of this type will undoubtedly be important for the development of chemistry’ but that this work ’asserts that frequency reflects reactivity for large databases. It is possible that this is true, but it is not proved here,’ and so ’the impact of this paper is likely to be in raising the profile of this approach to analysing chemistry, rather than in the details of its results’.   

Ross McLaren   

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