The Distal Effect of Electron-Withdrawing Groups and Hydrogen Bonding on the Stability of Peptide Enolates
Relative gas-phase carbon acidities have been computed for a series of acetamides, diketopiperazines, and linear dipeptides. The results show that N-electron-withdrawing substituents, protonation, and hydrogen bonding at amide nitrogen in these systems increase the acidity of both a C-H proton adjacent to the amide carbonyl and that of one proximal to the amide nitrogen. There is a good correlation between the magnitudes of the increases at the two positions, but the extent of the increase for...[Show more]
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|Source:||Journal of the American Chemical Society|
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