Probing Reactivity with External Forces: The Case of Nitroacetamides in Water

Abstract

Many computational methods have been applied to interpret and predict changes in reactivity by slight modifications of a given molecular scaffold. We describe a novel and simple method based on approximate density-functional theory of valence electrons that can be applied within a large high-performance computational infrastructure to probe such changes using a statistical sample of molecular configurations, including the solvent. All the used computational tools are fully open-source. Following our previous application, we are able to explain the high acidity of C-H bond at α position in nitro compounds when the amide linkage an ammonium group is inserted into the α substituent.

Keywords

• amides
• carbanions
• C-H acidity
• nitro-aci tautomerism
• molecular dynamics
• density-functional theory