An efficient computational model to predict protonation at the amide nitrogen and reactivity along the C–N rotational pathway. Issue 29 (13th March 2015)

• Record Type: Journal Article
• Authors: Szostak, Roman; Aubé, Jeffrey; Szostak, Michal
• Is Part Of: Chemical communications. Volume 51:Issue 29(2015)
• Page Start: 6395
• Page End: 6398
• Publication Date: 2015-03-13
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c5cc01034a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A computational model enabling prediction of protonation at the amide bond nitrogen atom along the C–N rotational pathway is reported. Abstract : N-Protonation of amides is critical in numerous biological processes, including amide bonds proteolysis and protein folding as well as in organic synthesis as a method to activate amide bonds towards unconventional reactivity. A computational model enabling prediction of protonation at the amide bond nitrogen atom along the C–N rotational pathway is reported. Notably, this study provides a blueprint for the rational design and application of amides with a controlled degree of rotation in synthetic chemistry and biology.