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Computer-Aided Solvent Screening

Approach could ease path to solvent selection when optimizing reaction conditions

by Jyllian Kemsley
September 23, 2013 | A version of this story appeared in Volume 91, Issue 38

Solvent effects play an essential role in determining chemical reaction rates and selectivities, but evaluating different solvents for a particular reaction has largely been a labor-intensive experimental process. A group of researchers led by Claire S. Adjiman and Amparo Galindo of Imperial College London has developed a computer-aided molecular design process that could save time by using a kinetic model to screen thousands of organic solvents for their effects on reaction rate constants (Nat. Chem. 2013, DOI: 10.1038/nchem.1755). Using a bimolecular nucleophilic substitution reaction as a test case, Adjiman, Galindo, and colleagues first calibrated the program using rate constants calculated with quantum mechanics for six solvents. They then looked at the effects of more than 1,300 solvents on the rate constant, performing full quantum mechanical computations for only nine solvents. The approach correctly predicted, for example, that nitromethane increased the reaction rate constant by 40% compared with acetonitrile. The screening framework can be adapted to evaluate reaction selectivity, as well as to incorporate factors such as solubility and toxicity, the researchers say.

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