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

ABSTRACT:

SUBMITTER: Vallejo Narvaez WE

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

REPOSITORIES: biostudies-literature

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

Vallejo Narváez Wilmer E WE Jiménez Eddy I EI Romero-Montalvo Eduardo E Sauza-de la Vega Arturo A Quiroz-García Beatriz B Hernández-Rodríguez Marcos M Rocha-Rinza Tomás T

Chemical science 20180405 19

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<sub>S</sub>) and H-bonded (C[double bond, length as m-dash]O<sub>HB</sub>) carbonyl groups in imides. Notwithstanding the considerable body of experimental and theoretical evidence supporting the JSIH, there are some computational studies which sugges ...[more]

PMID: 29896381

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