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Facile solid-state molecular assembly: the crystal structure of the unique 2∶2 proton-transfer oxine-salicylic acid compound

Graham SmithCentre for Instrumental and Developmental Chemistry, School of Physical and Chemical Sciences, Queensland University of Technology, G.P.O. Box 2434, Brisbane, AustraliaU.D. WermuthCentre for Instrumental and Developmental Chemistry, School of Physical and Chemical Sciences, Queensland University of Technology, G.P.O. Box 2434, Brisbane, AustraliaJonathan M. WhiteSchool of Chemistry, University of Melbourne, Parkville, Australia

2003en

ABI

Annotatsiya

The previously reported product from the solid-state reaction of quinolin-8-ol (oxine) with salicylic acid has been characterized using single crystal X-ray diffraction methods and confirmed as the discrete dimeric proton-transfer sandwich compound [(C9H8NO+)2(C7H5O3–)2] (1). As with similar compounds of carboxylic acids and oxine, protonation of the quinoline nitrogen occurs. However, in the case of 1, the two salicylate anions provide unusual duplex carboxylato-(O,O′) hydrogen-bonding bridges [(oxine)-N+H⋯O,O′(salicylate)⋯H′–O′-(oxine)′] which stitch together the pairs of π–π-associated oxine cations. This structure determination may provide a possible explanation of the mechanism involved in the facile solid-state reaction of oxine with salicylic acid.

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DOI: 10.1039/b210197c

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