No looking back for chemical manufacturing

In synthetic chemistry, a chemical reaction called nucleophilic substitution occurs when a nucleophile (electron-rich chemical species) replaces a leaving group (electron-poor fragment of an organic molecule).

Typically, the nucleophile attacks the organic molecule from the back—the side opposite of the location of the leaving group—where it is often blocked by other parts of the molecule, limiting the speed of the reaction.

Led by Prof Tan Choon Hong of NTU’s School of Physical and Mathematical Sciences, a group of chemists at NTU found that nucleophilic substitution reactions can also occur from the front, such that the nucleophile approaches the molecule from the same side as the leaving group.

Because the approach of the nucleophile is not sterically hindered, such reactions can be carried out much more quickly and efficiently. The discovery could fundamentally change the field of synthetic chemistry and thus how chemicals and pharmaceuticals are manufactured, the researchers say.

The article “An enantioconvergent halogenophilic nucleophilic substitution (SN2X) reaction” was published in Science (2019), DOI: 10.1126/science.aau7797. More details of the research can also be found at
The article appeared first in NTU’s research & innovation magazine Pushing Frontiers (issue #15, June 2019). 

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