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Molecules 2018, 23(11), 2859; https://doi.org/10.3390/molecules23112859

Amide Activation in Ground and Excited States

1
Institute of Materials and Environmental Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Budapest H-1117, Hungary
2
Laboratory of 3D Functional Imaging of Neuronal Networks and Dendritic Integration, Institute of Experimental Medicine, Hungarian Academy of Sciences, Budapest H-1083, Hungary
3
Institute of Chemistry, Eötvös University, Budapest H-1117, Hungary
4
Department of Chemistry, University of Toronto, Toronto, ON M5S 3H6, Canada
5
Department of Chemistry, Femtonics Inc., Budapest H-1094, Hungary
*
Author to whom correspondence should be addressed.
Academic Editor: Michal Szostak
Received: 4 October 2018 / Revised: 26 October 2018 / Accepted: 31 October 2018 / Published: 2 November 2018
(This article belongs to the Special Issue Amide Bond Activation)

Abstract

Not all amide bonds are created equally. The purpose of the present paper is the reinterpretation of the amide group by means of two concepts: amidicity and carbonylicity. These concepts are meant to provide a new viewpoint in defining the stability and reactivity of amides. With the help of simple quantum-chemical calculations, practicing chemists can easily predict the outcome of a desired process. The main benefit of the concepts is their simplicity. They provide intuitive, but quasi-thermodynamic data, making them a practical rule of thumb for routine use. In the current paper we demonstrate the performance of our methods to describe the chemical character of an amide bond strength and the way of its activation methods. Examples include transamidation, acyl transfer and amide reductions. Also, the method is highly capable for simple interpretation of mechanisms for biological processes, such as protein splicing and drug mechanisms. Finally, we demonstrate how these methods can provide information about photo-activation of amides, through the examples of two caged neurotransmitter derivatives. View Full-Text
Keywords: amide; activation; amidicity; carbonylicity; transamidation; acyl transfer; excited state amide; activation; amidicity; carbonylicity; transamidation; acyl transfer; excited state
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Kovács, E.; Rózsa, B.; Csomos, A.; Csizmadia, I.G.; Mucsi, Z. Amide Activation in Ground and Excited States. Molecules 2018, 23, 2859.

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