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

Molecular Cocrystals of Carboxylic Acids. I. The Crystal Structures of the Adducts of Indole-3-acetic-Acid With Pyridin-2(1H)-one, 3,5-Dinitrobenzoic Acid and 1,3,5-Trinitrobenzene

DE Lynch, G Smith, KA Byriel and CHL Kennard

Australian Journal of Chemistry 44(6) 809 - 819
Published: 1991

Abstract

Three molecular cocrystal adducts of the plant hormone indole-3-acetic acid ( iaa ) have been prepared and their structures determined by X-ray diffraction. They are indole-3-acetic acid-bis [pyridin-2(1H)-one] (1), indole-3-acetic acid-3,5-dinitrobenzoic acid (2) and indole-3-acetic acid-1,3,5-trinitrobenzene (3). Complexes (2) and (3), which may be prepared in a solid-state reaction, are orange and are structurally similar, having significant π-π indole -benzene ring interactions. However, the colourless complex (1) shows no π-π ring interactions. In complex (2), the 3,5-dinitrobenzoic acid molecules form hydrogen-bonded cyclic dimers (O…O, 2.64 Ǻ), while in (3) the indole-3-acetic acid molecules form dimers (O…O, 2.66 Ǻ). This feature contrasts with the structure of adduct (1) in which the pyridin-2(1H)-one molecules exist as dimers [N…O, 2.79, 2.74 Ǻ] analogous to those found in the parent compound.

https://doi.org/10.1071/CH9910809

© CSIRO 1991

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