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.
