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J Phys Chem B. 2008 Jul 3;112(26):7885-93. doi: 10.1021/jp8023292. Epub 2008 Jun 6.

Amidicity change as a significant driving force and thermodynamic selection rule of transamidation reactions. A synergy between experiment and theory.

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Department of Chemistry, University of Toronto, Toronto, ON, Canada.


Although essential in medicinal and industrial chemistry, transamidation reactions are still poorly understood mechanistically and in particular in terms of the extreme nature for their proceeding either very smoothly or not occurring at all. As yet, there exists no qualitative rule to predict the outcome of an amide interacting with an amine, with quantitative evaluations far from being established. In this paper we aim to clarify the thermodynamic selection rule and driving force of transamidation reactions based on amidicity value, measuring numerically the amide bond strength, toward providing a relatively simple protocol for practicing organic chemists to predict the outcome of an experiment. The change of amidicity over the course of a reaction made it possible to see that the process is favorable or unfavorable. This recently evaluated driving force of amidicity behaves analogously to the driving force of aromaticity in other organic reactions. This paper presents a successful comparison between empirical synthetic results and relevant computational characterizations, for a variety of transamidation reactions, all toward a synergy between experiments and theory. In this paper, we are re-examining experimentally and theoretically earlier experimental findings in relation to transamidation reactions and interpreting them from the aspect of amidicity change and stabilization enthalpies.


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