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Jared J. Gerschler, Kevin A. Wier, and David E. Hansen. 2007. Amide Bond Cleavage: The Acceleration Due to a 1,3-Diaxial Interaction with a Carboxylic Acid. Journal of Organic Chemistry 72: 654657. Full Article

To independently assess the contribution of ground-state pseudoallylic strain to the enormous rates of amide bond cleavage in tertiary amide derivatives of Kemp's triacid, we have studied four amide derivatives of (1α-3α-5β)-5-tert-butyl-1,3-cyclohexanedicarboxylic acid. Our results demonstrate that absent pseudoallylic strain, a 1,3-diaxial interaction of an amide with a carboxylic acid leads to only a 2400-fold increase in the rate of amide bond cleavage as compared with the rate of hydrolysis of an unactivated peptide bond.

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