What is it about?

A deformity in the electrostatic potential of chlorine, known as sigma-hole, allows chlorine to act as a positive charge and not as a negative one. We took advantage of this feature to remove chlorine atoms with negatively charged sulfur atoms. We have thus unlocked a chemical reactivity feature in CCl3 groups that can be versatilly used.

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Why is it important?

We can now use a new approach to reactivity of atoms in molecules which were thought to be negative as positive, this way we can now expand the toolbox of reactions for creating more complex molecules.


We now need to prove this approach can be extended to other atoms in the p-block to really create a powerful tool that expands the reactivity of main group element containing molecules.

Dr Joaquin Barroso-Flores
Universidad Nacional Autonoma de Mexico

Read the Original

This page is a summary of: Reactivity of electrophilic chlorine atoms due to σ-holes: a mechanistic assessment of the chemical reduction of a trichloromethyl group by sulfur nucleophiles, Physical Chemistry Chemical Physics, January 2016, Royal Society of Chemistry, DOI: 10.1039/c6cp04321f.
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