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Title: 2-(2,5-DICHLOROPHENYLHYDRAZONO)-GLUTARIC ACID (1) AND 2-(3,5-DICHLOROPHENYLHYDRAZONO)-GLUTARIC ACID (2)

Author
item ANTOLIC, SNJEZANA - RUDER BOSKOVIC INSTITUTE
item KOJIC-PRODIC, BISERKA - RUDER BOSKOVIC INSTITUTE
item Cohen, Jerry

Submitted to: Acta Crystallographica Section B: Structural Science
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 5/29/1996
Publication Date: N/A
Citation: N/A

Interpretive Summary: Indole-3-acetic acid (IAA) is an important plant hormone that is found in all plants and in all plant tissues. In some plants, such as fresh and canned peas and in faba beans, a halogen containing form of IAA has also been found. Synthesis of substituted compounds in which a specific hydrogen is changed to the halogen, fluorine, has been used in medicinal chemistry to alter the metabolic stability of target compounds without a major effect on the chemical properties. In order to understand the metabolism and activity of IAA and related compounds better, we developed a chemical synthesis for halogen substituted IAA. As part of this study, we characterized the intermediate compounds formed so that the chemical synthesis could be improved. These data will be useful to organic chemists, biochemists and chemical engineers interested in synthesis of similar compounds and may find application in the biorational design of growth regulating compounds and certain pharmaceuticals. These data may also prove important to food chemists and nutritionists interested in studies on the fate of halogenated IAA and its metabolites in human and animal diets.

Technical Abstract: A part of a systematic study of structure/activity correlations of the phytohormone indole-3-acetic acid, auxin, the series of monohalogenated and dihalogenated derivatives has been examined. During the preparation of the dihalogenated indole-3-acetic acids some intermediates were obtained and the crystal structures of these intermediates were solved. The compounds 2-(2,5dichlorophenylhydrazono)-glutaric acid [1] and 2-(3,5dichlorophenylhydrazono)-glutaric acid [2] are constitutional isomers which exhibit similar molecular geometry. The conformation about the bond N=C is E (both molecules). The same packing pattern was found in both structures. The hydrogen bonded dimers, formed around the inversion centers via O-H...O interactions of carboxyl groups, are connected into infinate chains. The intramolecular hydrogen bond N-H...Cl observed in the para-isomer (compound [1] only) contributes to the planarity of the molecule.