Amidicity

The amidicity scale is a computational method for calculating the strength of an amide bond in an organic compound on a linear scale.^[1] It is analogous to aromaticity.^[2] It is based on the computed enthalpy of hydrogenation when compared to the reference compounds dimethylacetamide and azaadamantane-2-one. If an amidicity value is close to 100%, then the compound has very good amidic character (and is perfect at 100%); if the value is close to, or below, 0%, then the compound has a lack of amidic character.^[1] The scale is not restricted to these values; compounds with weaker amide bonds than azaadamantane-2-one will have amidicities below 0%, whilst compounds with stronger amide bonds than dimethylacetamide will have amidicities of above 100%. If the amidicity value is altered during an acylation, then this will act as a key thermodynamic component of the reaction.^[1]

References

1 2 3 Z. Mucsi, A. Tsai, M. Szori, G. A. Chass, B. Viskolcz, I. G. Csizmadia (2007). "A Quantitative Scale for the Extent of Conjugation of the Amide Bond. Amidity Percentage as a Chemical Driving Force". J. Phys. Chem. A 111: 13245–13254. doi:10.1021/jp0759325.
↑ Z. Mucsi, B. Viskolcz, I. G. Csizmadia (2007). "A Quantitative Scale for the Degree of Aromaticity and Anti-aromaticity". J. Phys. Chem. A 111: 1123–1132. doi:10.1021/jp0657686.

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