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The distal effect of N-electron-withdrawing groups on the stability of peptide carbon radicals

Ho, Junming; Coote, Michelle; Easton, Christopher


The effect of electron-withdrawing substituents, hydrogen bonding and protonation at amide nitrogen on the stability of radicals formed by loss of either a distal CH adjacent to the amide carbonyl or one proximal to the amide nitrogen for a series of acetamides and diketopiperazines has been studied via high-level ab initio methods. These studies show that the effect is to destabilize the radicals formed by abstraction of the proximal hydrogens, typically by 10-20kJmol-1, and stabilize the...[Show more]

CollectionsANU Research Publications
Date published: 2011
Type: Journal article
Source: Australian Journal of Chemistry
DOI: 10.1071/CH11003


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