Amidicity

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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%.[citation needed] If the amidicity value is altered during an acylation, then this will act as a key thermodynamic component of the reaction.[1]

References[edit]

  1. ^ a b c 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. Bibcode:2007JPCA..11113245M. doi:10.1021/jp0759325. 
  2. ^ 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. Bibcode:2007JPCA..111.1123M. doi:10.1021/jp0657686.