Acidity and basicity interplay in amide and imide self-association.

ABSTRACT: Amides dimerise more strongly than imides despite their lower acidity. Such an unexpected result has been rationalised in terms of the Jorgensen Secondary Interactions Hypothesis (JSIH) that involves the spectator (C[double bond, length as m-dash]O_S) and H-bonded (C[double bond, length as m-dash]O_HB) carbonyl groups in imides. Notwithstanding the considerable body of experimental and theoretical evidence supporting the JSIH, there are some computational studies which suggest that there might be other relevant intermolecular interactions than those considered in this model. We conjectured that the spectator carbonyl moieties could disrupt the resonance-assisted hydrogen bonds in imide dimers, but our results showed that this was not the case. Intrigued by this phenomen

SUBMITTER: Vallejo Narvaez WE 

PROVIDER: S-EPMC5956980 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature