The amidicity scale is a

computational method Computation is any type of arithmetic or non-arithmetic calculation that follows a well-defined model (e.g., an algorithm). Mechanical or electronic devices (or, historically, people) that perform computations are known as '' computers''. An e ...

for calculating the strength of an

amide bond In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is p ...

in an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

on a linear scale. It is analogous to aromaticity. It is based on the computed

enthalpy of hydrogenation The standard enthalpy of reaction (denoted \Delta_ H^\ominus or \Delta H_^\ominus) for a chemical reaction is the difference between total reactant and total product molar enthalpies, calculated for substances in their standard states. This can in ...

when compared to the reference compounds

dimethylacetamide Dimethylacetamide (DMAc or DMA) is the organic compound with the formula CH3C(O)N(CH3)2. This colorless, water-miscible, high-boiling liquid is commonly used as a polar solvent in organic synthesis. DMA is miscible with most other solvents, altho ...

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. The scale is not restricted to these values; compounds with weaker amide bonds than azaadamantane-2-one will have amidicities below 0%, while compounds with stronger amide bonds than dimethylacetamide will have amidicities of above 100%. If the amidicity value is altered during an

acylation In chemistry, acylation (or alkanoylation) is the chemical reaction in which an acyl group () is added to a compound. The compound providing the acyl group is called the acylating agent. Because they form a strong electrophile when treated with ...

, then this will act as a key

thermodynamic Thermodynamics is a branch of physics that deals with heat, work, and temperature, and their relation to energy, entropy, and the physical properties of matter and radiation. The behavior of these quantities is governed by the four laws of ther ...

component of the reaction.

References

Amidicity Theoretical chemistry {{Computer-chemistry-stub