HYDROGEN-DEUTERIUM EXCHANGE IN LACTAMS

The kinetics of hydrogen-deuterium exchange have been measured for three cis lactams (butyrolactam, valerolactam, and caprolactam), the cis-trans lactam (caprylactam), and a trans amide (N-methylacetamide) in deuterium oxide solution. Exchange rates and activation energies (12-15 kcal/mole) are comparable for both the cis and trans configurations. Furthermore, activation energies are of a similar magnitude as those for other model peptides, polypeptides, and proteins. © 1969, American Chemical Society. All rights reserved.