The role of molecular structure in determining the acidity of nitroacetoamides in water.

What is it about?

C-H bonds are usually assumed not perturbed by polar O-H bonds. But in exceptional cases, liquid water can act on a C-H bond, providing its heterolytic dissociation witnessed by the protons ejected from the organic solute into the water. This happens when C-H bonds are surrounded by groups that properly attract water from the bulk towards the organic solute, where water plays a special role. It is like having a small lab condensed over a small organic compound in a water droplet: this unexpected role of water is reported in the article.

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Why is it important?

In a molecular structure, the acidity can be modulated tuning its idrophilicity