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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Hydrogen bonding in organic compounds. II. Amine-cabonyl interactions

AN Hambly and J Bonnyman

Australian Journal of Chemistry 11(4) 529 - 537
Published: 1958

Abstract

A comparison of the infra-red spectra of typical aromatic compounds, with a primary amine group adjacent to a carbonyl group, with the spectra of related compounds, shows that, in the former, weak hydrogen bonding occurs between the two groups. The strength of the bonds formed is in the order : 1-aminoanthraquinone > 2-amino-acetophenone > methyl anthranilate, and the changes in carbonyl frequency are comparable with those of the symmetric NH2 stretching frequency. Stronger hydrogen bonds are formed in corresponding ortho-acetamido compounds. A brief study of the NH2 stretching frequencies of o-nitroamines in dioxan solution shows that there is considerable interaction between solute and solvent but this cannot be definitely attributed to intermolecular hydrogen bonding.

https://doi.org/10.1071/CH9580529

© CSIRO 1958

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